Heterocyclylalkylpiperidine derivatives, their preparation and compositions containing them

ABSTRACT

Heterocyclylalkylpiperidine derivatives of general formula (I)  
                 
 
     in their enantiomeric or diastereoisomeric forms or mixtures of these forms, and/or, where appropriate, in their syn or anti form or a mixture thereof, as well as any salt thereof.

[0001] The present application claims priority of U.S. ProvisionalApplication No. 60/255,145, filed Dec. 14, 2000, and of French PatentApplication No. FR 00 14738, filed Nov. 15, 2000, all of which arespecifically incorporated by reference herein.

[0002] The present invention relates to heterocyclylalkyl-piperidinederivatives of general formula:

[0003] which are active as antimicrobial agents. The invention alsorelates to their preparation and to compositions containing them.

[0004] Patent applications WO 99/37635 and WO 00/43383 discloseantimicrobial quinolylpropylpiperidine derivatives of general formula:

[0005] in which the radical R₁ is especially (C1-6) alkoxy, R₂ ishydrogen, R₃ is in position −2 or −3 and represents (C1-6) alkyl whichmay optionally be substituted with from 1 to 3 substituents chosen fromthiol, halogen, alkylthio, trifluoromethyl, carboxyl, alkyloxycarbonyl,alkylcarbonyl, alkenyloxycarbonyl, alkenylcarbonyl, hydroxyl optionallysubstituted with alkyl, etc., R₄ is a group —CH₂—R₅ for which R₅ isselected from alkyl, hydroxyalkyl, alkenyl, alkynyl, tetrahydrofuryl,optionally substituted phenylalkyl, optionally substitutedphenylalkenyl, optionally substituted heteroarylalkyl, optionallysubstituted heteroaryl, etc., n is 0 to 2, m is 1 or 2 and A and B areespecially oxygen, sulfur, sulfinyl, sulfonyl, NR₁₁, CR₆R₇ for which R₆and R₇ represent H, thiol, alkylthio, halo, trifluoromethyl, alkenyl,alkenylcarbonyl, hydroxyl, amino, and Z₁ to Z₅ are N or CR_(1a), etc.

[0006] These products show antimicrobial activity. However, noderivative disubstituted in position −4 of the piperidine had beensynthesized hitherto and consequently no biological activity had beendiscovered for such products either.

[0007] Since slight modifications to the structures already known canresult in large variations in activity, it was not obvious thatderivatives disubstituted in position −4 of the piperidine would alsohave antibacterial activity.

[0008] European patent application EP 30044 discloses quinolinederivatives which are useful as cardiovascular agents, corresponding tothe general formula:

[0009] in which R₁ is especially alkyloxy, A-B is —CH₂— CH₂—,—CHOH—CH₂—, —CH₂—CHOH—, —CH₂—CO— or —CO—CH₂—, R₁ is H, OH or alkyloxy,R₂ is ethyl or vinyl, R₃ is especially alkyl, hydroxyalkyl, cycloalkyl,hydroxyl, alkenyl, alkynyl, tetrahydrofuryl, phenylalkyl, optionallysubstituted diphenylalkyl, optionally substituted phenylalkenyl,optionally substituted benzoyl or benzoylalkyl, optionally substitutedheteroaryl or heteroarylalkyl, and Z is H or alkyl or forms with R₃ acycloalkyl radical.

[0010] It has now been found, and this forms the subject of the presentinvention, that the products of general formula (I) for which:

[0011] X₁, X₂, X₃, X₄ and X₅ represent, respectively, >C—R′₁ to >C—R′₅,or alternatively not more than one of them represents a nitrogen atom,

[0012] R₁, R′₁, R′₂, R′₃, R′₄ and R′₅ are identical or different andrepresent a hydrogen or halogen atom or an alkyl, cycloalkyl, phenyl,phenylthio, mono- or bicyclic aromatic heterocyclyl or heterocyclylthio,hydroxyl, alkyloxy, trifluoromethoxy, alkylthio, trifluoromethylthio,cycloalkyloxy, cycloalkylthio, cyano, carboxyl, alkyloxycarbonyl,cycloalkyloxycarbonyl, —NRaRb or —CONRaRb radical (for which Ra and Rbcan represent hydrogen, alkyl, cycloalkyl, phenyl, mono- or bicyclicaromatic heterocyclyl or Ra and Rb form, together with the nitrogen atomto which they are attached, a 5- or 6-membered heterocycle which canoptionally contain another heteroatom chosen from O, S, and N and, whereappropriate, bearing an alkyl, phenyl or mono- or bicyclic aromaticheterocyclyl substituent on the nitrogen atom or, where appropriate, thesulfur atom of which is oxidized in the form of sulfinyl or sulfonyl),or represent a methylene radical substituted with fluoro, hydroxyl,alkyloxy, alkylthio, cycloalkyloxy, cycloalkylthio, phenyl, mono- orbicyclic aromatic heterocyclyl, carboxyl, alkyloxycarbonyl,cycloalkyloxycarbonyl, —NRaRb or —CONRaRb for which Ra and Rb aredefined as above, or represent phenoxy, heterocyclyloxy, benzyloxy,heterocyclylmethyloxy, or alternatively R₁ can also representdifluoromethoxy, or a radical of structure —C_(m)F_(2m+1),—SC_(m)F_(2m+1) or —OC_(m)F_(2m+1) for which m is an integer from 1 to6, or alternatively R′₅ can also represent trifluoroacetyl,

[0013] R₂ represents carboxyl, alkyloxycarbonyl, cycloalkyloxycarbonyl,cyano, —CONRaRb (for which Ra and Rb represent, respectively, hydrogen,alkyl, cycloalkyl, phenyl, mono- or bicyclic aromatic heterocyclyl, orRa or Rb represents hydroxyl, alkyloxy, cycloalkyloxy, or Ra and Rbform, together with the nitrogen atom to which they are attached, a 5-or 6-membered heterocycle which can optionally contain anotherheteroatom chosen from O, S and N and, where appropriate, bearing analkyl, phenyl or mono- or bicyclic aromatic heterocyclyl substituent onthe nitrogen atom or, where appropriate, the sulfur atom of which isoxidized in the form of sulfinyl or sulfonyl), or R₂ representshydroxymethyl, alkyl containing 1 or 2 carbon atoms substituted withcarboxyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, cyano or —CONRaRb forwhich Ra and Rb are defined as above, or R₂ represents a radical ofstructure —CF₂-Rc, —C(CH₃)₂-Rc, —CO-Rc, —CHOH-Rc, —C(cycloalkyl)-Rc, or—CH═CH-Rc for which Rc is carboxyl, alkyloxycarbonyl,cycloalkyloxycarbonyl, or —CONRaRb for which Ra and Rb are defined asabove,

[0014] R₃ represents a phenyl, mono- or bicyclic aromatic heterocyclylor alk-R°₃ radical for which alk is an alkyl radical and R°₃ representshydrogen, halogen, hydroxyl, alkyloxy, alkylthio, alkylsulfinyl,alkylsulfonyl, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy,cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, cycloalkylamino,N-cycloalkyl-N-alkylamino, —N-(cycloalkyl)₂, acyl, cycloalkylcarbonyl,phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl,phenylamino, N-alkyl-N-phenylamino, N-cycloalkyl-N-phenylamino,—N-(phenyl)₂, phenylalkyloxy, phenylalkylthio, phenylalkylsulfinyl,phenylalkylsulfonyl, phenylalkylamino, N-alkyl-N-phenylaminoalkyl,N-cycloalkyl-N-phenylalkylamino, benzoyl, mono- or bicyclic aromaticheterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylsulfinyl,heterocyclylsulfonyl, heterocyclylamino, N-alkyl-N-heterocyclylamino,N-cycloalkyl-N-heterocyclylamino, heterocyclylcarbonyl,heterocyclylalkyloxy, heterocyclylalkylthio, heterocyclylalkylsulfinyl,heterocyclylalkylsulfonyl, heterocyclylalkylamino,N-alkyl-N-heterocyclylaminoalkyl, N-cycloalkyl-N-heterocyclylaminoalkyl,(the heterocyclyl portions mentioned above being mono- or bicyclicaromatic), carboxyl, alkyloxycarbonyl, —NRaRb or —CO—NRaRb for which Raand Rb are defined as above in the definition of R₂, or alternativelyR°₃ represents —CR′b=CR′c-R′a for which R′a represents phenyl,phenylalkyl, heterocyclyl or heterocyclylalkyl in which the heterocyclylportion is mono- or bicyclic aromatic, phenoxyalkyl, phenylthioalkyl,phenylsulfinylalkyl, phenylsulfonylalkyl, phenylaminoalkyl,N-alkyl-N-phenylaminoalkyl, heterocyclyloxyalkyl, heterocyclylthioalkyl,heterocyclylsulfinylalkyl, heterocyclylsulfonylalkyl,heterocyclylaminoalkyl, N-alkyl-N-heterocyclylaminoalkyl,heterocyclylthio, heterocyclylsulfinyl, heterocyclylsulfonyl, (theheterocyclyl portions mentioned above being mono- or bicyclic aromatic),phenylthio, phenylsulfinyl, phenylsulfonyl, and for which R′b and R′crepresent hydrogen, alkyl or cycloalkyl, or alternatively R°₃ representsa radical —C≡C-Rd for which Rd is alkyl, phenyl, phenylalkyl,phenoxyalkyl, phenylthioalkyl, N-alkyl-N-phenylaminoalkyl, mono- orbicyclic aromatic heterocyclyl, heterocyclylalkyl, heterocyclyloxyalkyl,heterocyclylthioalkyl, heterocyclylaminoalkyl,N-alkyl-N-heterocyclylaminoalkyl, (the heterocyclyl portions mentionedabove being mono- or bicyclic aromatic), or alternatively R°₃ representsa —CF₂-phenyl or mono- or bicyclic aromatic —CF₂-heterocyclyl radical,

[0015] Y represents a radical >CH—Re for which Re is hydrogen, fluoro,hydroxyl, alkyloxy, cycloalkyloxy,-carboxyl, alkyloxycarbonyl,cycloalkyloxycarbonyl, —NRaRb or —CO—NRaRb for which Ra and Rb aredefined as above for R₂ or one represents a hydrogen atom and the otherrepresents an alkyloxycarbonyl, acyl, cycloalkylcarbonyl, benzoyl orheterocyclylcarbonyl radical in which the heterocyclyl portion is mono-or bicyclic aromatic, or alternatively Y represents a difluoromethylene,carbonyl, hydroxyiminomethylene, alkyloxyiminomethylene orcycloalkyloxyiminomethylene radical or a 1,1-cycloalkylene radicalcontaining 3 to 6 carbon atoms; and

[0016] n is an integer from 0 to 4;

[0017] it being understood that the phenyl, benzyl, benzoyl orheterocyclyl radicals or portions mentioned above may optionally besubstituted on the ring with 1 to 4 substituents chosen from halogen,hydroxyl, alkyl, alkyloxy, alkyloxyalkyl, haloalkyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, carboxyl, alkyloxycarbonyl,cyano, alkylamino, —NRaRb for which Ra and Rb are defined as above,phenyl, hydroxyalkyl, alkylthioalkyl, alkylsulfinylalkyl andalkylsulfonylalkyl,

[0018] in their enantiomeric or diastereoisomeric forms or mixtures ofthese forms, and/or, where appropriate, in their syn or anti form or amixture thereof, as well as the salts thereof, are powerfulantibacterial agents.

[0019] It is understood that the alkyl or acyl radicals and portionscontain (except where especially mentioned) 1 to 10 carbon atoms in astraight or branched chain and that the cycloalkyl radicals contain 3 to6 carbon atoms.

[0020] It is also understood that the radicals which represent or bear ahalogen atom represent a halogen chosen from fluorine, chlorine, bromineand iodine, wherein fluorine is an embodiment of particular interest.

[0021] In the above general formula, when the radicals represent or beara mono- or bicyclic aromatic heterocyclyl substituent, this substituentcontains 5 to 10 chain members and may be chosen (in a nonlimitingmanner) from thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl,thiadiazolyl, oxadiazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrazinyl,pyrimidinyl, indolyl, benzothienyl, benzofuryl indazolyl,benzothiazolyl, naphthyridinyl, quinolyl, isoquinolyl, cinnolyl,quinazolyl, quinoxalyl, benzoxazolyl and benzimidazolyl which mayoptionally be substituted with the substituents listed above.

[0022] According to the invention, the products of general formula (I)may be obtained by coupling the chain R₃ with theheterocyclylalkylpiperidine derivative of general formula:

[0023] in which X₁, X₂, X₃, X₄, X₅, R₁, R₂, Y and n are defined asabove, and R₂ is protected when it bears a carboxyl or amino radical,optionally followed by removal of the acid-protecting oramine-protecting radical, optional separation of the enantiomeric ordiastereoisomeric forms and/or, where appropriate, of the syn or antiforms and optional conversion of the product obtained into a salt.

[0024] The coupling of the chain R₃ with the piperidine isadvantageously carried out by the action of a derivative of generalformula (IIa):

R₃—X   (IIa)

[0025] in which R₃ is defined as above and X represents a halogen atom,a methylsulfonyl radical, a trifluoromethylsulfonyl radical or ap-toluenesulfonyl radical, working in anhydrous medium, which isoptionally inert (for example nitrogen or argon) in an organic solventsuch as an amide (for example dimethylformamide), a ketone (for exampleacetone) or a nitrile (for example acetonitrile) in the presence of abase such as an organonitrogen base (for example triethylamine) or amineral base (alkaline carbonate, for example potassium carbonate) at atemperature of between 20° C. and the reflux temperature of the solvent.It is understood that the nitrogen atom of the piperidine in thederivative of general formula (II) is optionally protected according tothe usual methods which do not affect the rest of the molecule or thereaction; for example, the protection is carried out by a protectingradical chosen from t-butoxycarbonyl and benzyloxycarbonyl.

[0026] In one embodiment of the invention, a derivative of generalformula (IIa) for which X is a bromine or iodine atom is reacted.

[0027] When R₃ is a phenyl radical, it is also possible to act on theiodo or bromo derivative R₃—X in the presence of a palladium catalystaccording to the method described in J. Org. Chem., 6066 (1997) or Tet.Lett., 6359 (1997). The palladium catalyst may be chosen fromtris(dibenzylideneacetone)dipalladium, and palladium diacetate with aligand such as 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl or2-(di-t-butylphosphino)biphenyl, for example, a base such as sodiumtert-butoxide or cesium carbonate in a solvent such as tetrahydrofuran,tetraglyme or toluene, optionally in the presence of a crown ether suchas 18-C-6 (1,4,7,10,13,16-hexaoxacyclooctadecane). The reaction iscarried out at a temperature of between 20° C. and 110° C.

[0028] When R₃ represents a radical -alk-R°₃ for which alk is an alkylradical and R°₃ represents —C≡C-Rd in which Rd is phenyl, phenylalkyl,heterocyclyl or mono- or bicyclic aromatic heterocyclylalkyl, optionallyone may couple an alkynyl halide: HC≡C-alk-X for which alk is defined asabove and X is a halogen atom, and then may substitute the chain with aphenyl, phenylalkyl, heterocyclyl or heterocyclylalkyl radical.

[0029] In this alternative, the addition of the alkynyl chain is carriedout using an alkynyl halide HC≡C-alk-X for which X is optionally abromine atom, under the conditions listed above for the coupling of thechain R₃, in the presence or absence of an alkali metal iodide such as,for example, potassium iodide or sodium iodide.

[0030] The substitution with a phenyl or heterocyclyl radical is carriedout by the action of a halide derived from the cyclic radical to besubstituted, in the presence of triethylamine, in anhydrous medium in asolvent such as an amide (for example dimethylformamide) or a nitrile(for example acetonitrile) and in the presence of a palladium salt suchas, for example, tetrakis(triphenylphosphine)palladium and cuprousiodide, at a temperature of between 20° C. and the reflux temperature ofthe solvent.

[0031] The substitution with a phenylalkyl or heterocyclylalkyl radicalis carried out by the action of the corresponding halide, in basicmedium, for example in the presence of potassium hydride or sodiumhydride or n-butyllithium, in a solvent such as an ether(tetrahydrofuran) or an amide (dimethylformamide) at a temperature ofbetween −60° C. and the boiling point of the reaction medium.

[0032] It is understood that, if the alkyl radicals represented by R₃bear carboxyl or amino substituents, these substituents are protectedbeforehand then freed after the reaction. The process is performedaccording to the usual methods which do not affect the rest of themolecule, in particular according to the methods described by T. W.Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis (2^(nd)edition), A. Wiley—Interscience Publication (1991), or by McOmie,Protective Groups in Organic Chemistry, Plenum Press (1973).

[0033] The protected carboxyl radical borne by R₂ may be chosen fromreadily hydrolyzable esters. Examples are the methyl, benzyl, andtert-butyl esters, or the phenyl propyl or allyl esters. The protectionof the carboxyl radical is optionally carried out at the same time asthe reaction.

[0034] Where appropriate, the amino radical is protected using the usualprotecting radicals mentioned in the above references.

[0035] These protecting radicals are installed and removed according tothe usual methods, mentioned above for R₃.

[0036] When R₃ represents a radical-alk-R°₃ for which alk is an alkylradical and R°₃ represents a phenoxy, phenylthio, phenylamino,heterocyclyloxy, heterocyclylthio or heterocyclylamino radical in whichthe heterocyclyl portion is aromatic, optionally the chain may beconstructed step by step, by first condensing a chain HO-alk-X, forwhich X is a halogen atom (optionally iodine), under the conditionsdescribed above for the reaction of the product of general formula(IIa), and then by converting the hydroxyalkyl chain into a haloalkyl,methanesulfonylalkyl or p-toluenesulfonyl-alkyl chain, and finally byreacting, in basic medium, an aromatic derivative of structure Ar—ZH forwhich AR is an aromatic phenyl or heterocyclyl radical and Z is asulfur, oxygen or nitrogen atom.

[0037] The conversion of the hydroxylated chain into a haloalkyl orp-toluenesulfonyl chain is carried out according to the usual methods ofhalogenation or sulfonylation, especially by reacting a halogenatingagent, for instance, thionyl chloride, halophosphorus derivatives: forexample phosphorus trichloride or tribromide or a sulfonylating agentsuch as, for example, methanesulfonyl chloride, p-toluenesulfonylchloride or trifluoromethanesulfonic anhydride. The reaction is carriedout in an organic solvent, for instance a chlorinated solvent (forexample dichloromethane or chloroform), at a temperature of between 0°C. and 60° C. In certain cases, it may be advantageous to work in thepresence of a base, for instance pyridine or triethylamine.

[0038] The reaction of the aromatic derivative Ar—ZH is advantageouslycarried out as described above for the action of the derivative ofgeneral formula (IIa), in the presence of a base, for example such as anitrogenous base, in an organic solvent such as an amide (for exampledimethylformamide), a ketone (for example acetone) or a nitrile (forexample acetonitrile), in the presence of a base such as a nitrogenousorganic base (for example triethylamine) or a mineral base (alkali metalcarbonate: for example potassium carbonate) at a temperature of between20° C. and the reflux temperature of the reaction mixture. It may beadvantageous to work in the presence of potassium iodide.

[0039] According to the invention, the heterocyclyl-alkylpiperidinederivatives of general formula (II) may be prepared according to thecoupling method described below, and then where appropriate convertedaccording to one of the methods {circle over (1)} to {circle over (9)}below, via a subsequent operation starting with one of the derivativesof general formula (II) already obtained, to prepare the derivativescorresponding to the various alternatives of Y and/or of R₁, R′₁, R′₂,R′₃, R′₄ or R′₅.

[0040] It is understood that when carboxylic acid radicals are presenton the molecule, these radicals are protected beforehand and then freedafter the reaction according to the usual methods which do not affectthe rest of the molecule, especially according to the methods mentionedin the references cited above. It is also understood that, prior to thereactions which may interfere with the amine of the piperidine in thederivative of general formula (II), this amine is protected, and thenfreed after the reaction. The protection is carried out according to theusual methods, as specified above, especially via a t-butoxycarbonyl orbenzyloxycarbonyl radical.

[0041] According to the invention, the preparation of the products ofgeneral formula (II) for which Re in Y is a hydrogen atom is carried outby coupling a heterocyclic derivative of general formula:

[0042] in which R₁, X₁, X₂, X₃, X₄ and X₅ are defined as above and Halrepresents a halogen atom, with a piperidine derivative of generalformula:

[0043] in which Rz is a protecting radical and R″₂ is defined as aboveor represents a protected radical if R₂ represents or bears a carboxylicacid function, followed by removal of the protecting radicals and/orfollowed by conversion, via a subsequent operation, of the substituentsof the bicycle of the heterocyclylalkylpiperidine derivative of generalformula (II) thus obtained, to give the expected derivative bearing theradical R₁, R′₁, R′₂, R′₃, R′₄, or R′₅, and, where appropriate, removalof the protecting radical(s) still present on the molecule.

[0044] The radical Rz may be any protecting group for the nitrogen atomwhich is compatible with the reaction (for example t-butyloxycarbonyl orbenzyloxycarbonyl). The protecting groups for the acid functions arechosen from the usual groups whose installation and removal do notaffect the rest of the molecule, especially those mentioned in thereferences cited above.

[0045] The reaction is carried out by the successive action of anorganoborane (for example 9-borabicyclo-[3.3.1]nonane) in a solvent suchas an ether (for example tetrahydrofuran or dioxane) at a temperature ofbetween −20° C. and 20° C., and then of the bicyclic derivative ofgeneral formula (III) wherein Hal optionally represents a bromine oriodine atom or a chlorine atom, by analogy with the methods described bySuzuki et al., Pure and Appl. Chem., 57, 1749 (1985). The reaction isgenerally carried out in the presence of a palladium salt (for examplediphenylphosphinoferrocenepalladium chloride) and of a base such aspotassium phosphate, at a temperature of between 20° C. and the refluxtemperature of the solvent.

[0046] {circle over (1)} The heterocyclylalkylpiperidines of generalformula (II) for which Re in Y represents a hydroxyl radical may beprepared by oxidation in basic medium of the correspondingheterocyclylalkylpiperidine derivative of general formula (II) for whichRe in Y is a hydrogen atom. The oxidation is carried out by the actionof oxygen, optionally in an inert solvent such as dimethyl sulfoxide inthe presence of tert-butanol and of a base such as potassiumtert-butoxide or sodium tert-butoxide at a temperature of between 0° C.and 100° C.

[0047] The heterocyclylalkylpiperidine derivative for which Re in Y is afluorine atom is prepared by fluorination starting with a derivative forwhich Re is hydroxyl. The reaction is carried out in the presence of asulfur fluoride [for example in the presence of an aminosulfurtrifluoride (diethylaminosulfur trifluoride (Tetrahedron, 44, 2875(1988), bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor®), ormorpholinosulfur trifluoride, for example) or alternatively in thepresence of sulfur tetrafluoride (J. Org. Chem., 40, 3808 (1975);alternatively, the fluorination reaction can also be carried out using afluorinating agent such as hexafluoropropyldiethylamine (JP 2 039 546)or N-(2-chloro-1,1,2-trifluoroethyl)diethylamine.

[0048] The process is performed in an organic solvent such as achlorinated solvent (for example dichloromethane, dichloroethane orchloroform), or in an ether (for example tetrahydrofuran or dioxane), ata temperature of between −78° C. and 40° C., or optionally between 0° C.and 30° C. It is advantageous to work in inert medium (especially argonor nitrogen).

[0049] The heterocyclylalkylpiperidine derivative of general formula(II) for which Re in Y is an alkyloxy or cycloalkyloxy radical isprepared by the action of an alkyl or cycloalkyl halide on thecorresponding derivative of general formula (II) for which Re ishydroxyl. The reaction is generally carried out using the bromide orchloride, in an inert solvent such as N,N-dimethylformamide or dimethylsulfoxide, in the presence of an acid acceptor such as a trialkylamine(for example triethylamine) or an alkali metal hydride (for examplesodium hydride), at a temperature of between 20° C. and 100° C.

[0050] The heterocyclylalkylpiperidine derivative of general formula(II) for which Y is a carbonyl radical may be prepared by oxidation ofthe corresponding derivative of general formula (II) for which Re in Yis a hydroxyl radical. This oxidation is carried out, for example, usingpotassium permanganate optionally in a solution of sodium hydroxide (forexample 3N sodium hydroxide), at a temperature of between −20° C. and20° C., or alternatively by the action of oxalyl chloride in thepresence of dimethyl sulfoxide, followed by the addition of an aminesuch as triethylamine, in an inert solvent such as dichloromethane ordimethyl sulfoxide, at a temperature of between −60° C. and 20° C., byanalogy with the method described by D. Swern et al., J. Org. Chem., 44,4148 (1979).

[0051] The heterocyclylalkylpiperidine derivative of general formula(II) for which Y is a difluoromethylene radical may be prepared bydihalogenation of the product of general formula (II) for which Y iscarbonyl, under conditions analogous to those of the fluorinationdescribed above.

[0052] The heterocyclylalkylpiperidine derivative of general formula(II) for which Y is a hydroxyiminomethylene radical may be prepared bythe action of hydroxylamine on a derivative of general formula (II) forwhich Y is a carbonyl radical. The reaction is generally carried out inan inert solvent such as an alcohol (methanol or ethanol) and optionallyin the presence of sodium hydroxide (for example 1N sodium hydroxide),at a temperature of between 0° C. and the boiling point of the reactionmixture.

[0053] The heterocyclylalkylpiperidine derivative of general formula(II) for which Y is an alkyloxyiminomethylene orcycloalkyloxyiminomethylene radical may be prepared by the action of analkyl or cycloalkyl halide on the corresponding derivative of generalformula (II) for which Y is hydroxyiminomethylene. The reaction isgenerally carried out in an inert solvent such as N,N-dimethylformamideor dimethyl sulfoxide, in the presence of an acid acceptor such as atrialkylamine (for example triethylamine) or an alkali metal hydride(for example sodium hydride), at a temperature of between 20° C. and100° C. A bromide is one example of interest in the present invention.

[0054] The heterocyclylalkylpiperidine derivative of general formula(II) for which Re in Y is a radical —NRaRb may be prepared from thecorresponding tosyloxy derivative by the action of an amine HNRaRb (or,where appropriate, of ammonia when Re is —NH₂) in an inert solvent suchas N,N-dimethylformamide or dimethyl sulfoxide, at a temperature ofbetween 20° C. and the boiling point of the reaction mixture. Whenammonia is reacted, the process is optionally performed under pressure(2 to 20 atmospheres) at a temperature of between 20° C. and 100° C.When the process is performed using an amine HNRaRb, the reaction isoptionally carried out in the presence of a base such as a trialkylamine(for example triethylamine), pyridine or an alkali metal hydride (forexample sodium hydride).

[0055] The derivative for which Re in Y is tosyloxy is obtained from theproduct of general formula (II) for which Re in Y is hydroxyl, by theaction of tosyl chloride in pyridine, at a temperature of between −10°C. and 20° C.

[0056] The heterocyclylalkylpiperidine derivative of general formula(II) for which Re in Y is a carboxyl radical may be prepared by theaction of an alkaline cyanide on the corresponding tosyloxy derivative,in an organic solvent such as dimethylformamide or dimethyl sulfoxide orin aqueous-organic medium, for example a water-alcohol mixture, at atemperature of between 0° C. and the boiling point of the reactionmixture, followed by hydrolysis of the nitrile obtained by the action ofa strong acid such as hydrochloric acid, and optionally of a loweraliphatic alcohol, at a temperature of between 0° C. and the boilingpoint of the reaction mixture. Sodium cyanide or potassium cyanide areboth options according to the present invention.

[0057] The heterocyclylalkylpiperidine derivative of general formula(II) for which Re in Y is an alkyloxycarbonyl or cycloalkyloxycarbonylor —CO—NRaRb radical may be prepared by the action, respectively, of thealcohol or of the corresponding amine on the derivative of generalformula (II) for which Re in Y is a carboxyl radical. The reaction iscarried out in the presence of a coupling agent such as a carbodiimide(for example N,N′-dicyclohexylcarbodiimide) or N,N′-carbonyldiimidazole,in an inert solvent such as an ether. (for example tetrahydrofuran ordioxane), an amide (N,N-dimethylformamide), a chlorinated solvent (forexample methylene chloride, 1,2-dichloroethane or chloroform) ordimethyl sulfoxide, at a temperature of between 0° C. and the refluxtemperature of the reaction mixture.

[0058] {circle over (2)} The heterocyclylalkylpiperidine derivative ofgeneral formula (II) for which Y is a 1,1-cycloalkylene radical may beprepared by the action, in basic medium, of a product of structureHal-Alk-Hal for which Alk is an alkylene radical corresponding to theexpected cycloalkylene, on a heterocyclylalkylpiperidine derivative forwhich Re in Y is a hydrogen atom. The reaction is generally carried outin an inert solvent such as N,N-dimethylformamide or dimethyl sulfoxide,in the presence of an acid acceptor such as an alkali metal hydride (forexample sodium hydride), at a temperature of between 20° C. and 100° C.

[0059] {circle over (3)} The heterocyclylalkylpiperidine derivatives ofgeneral formula (II) for which one from among R₁, R′₁, R′₂, R′₃, R′₄ andR′₅ represents an alkyl, cycloalkyl, phenyl, heterocyclyl, benzyl orheterocyclylmethyl radical may be prepared by the action of a boronderivative of structure R′_(i)B(OH)₂ (R′i meaning one of thesubstituents R₁, R′₁, R′₂, R′₃, R′₄ or R′₅) or of 9-alkyl- (or9-cycloalkyl)-9-borabicyclo[3.3.1]nonane structure on a derivative ofgeneral formula (II) for which the substituent R′_(i) is a bromine,iodine or chlorine atom, by analogy with the methods described by F.Diederich and P. J. Stang, Metal Catalysed Cross-coupling Reactions,Wiley-VCH, (1997) in the presence of a palladium salt (for exampletetrakis(triphenylphosphine) or diphenylphosphinoferrocenepalladiumchloride) and of a base such as potassium phosphate, in an inert solventsuch as an amide (for example N,N-dimethylformamide), an ether (forexample tetrahydrofuran) or a nitrile (for example acetonitrile), at atemperature of between 20° C. and the reflux temperature of the reactionmixture.

[0060] {circle over (4)} The heterocyclylalkylpiperidine derivatives ofgeneral formula (II) for which one from among R₁, R′₁, R′₂, R′₃, R′₄ andR′₅ represents a radical —NRaRb may be prepared by the action of anamine HNRaRb on a derivative of general formula (II) for which thesubstituent R′_(i) (R′i meaning one of the substituents R₁, R′₁, R′₂,R′₃, R′₄ or R′₅) is a bromine, iodine or chlorine atom, by analogy withthe methods described in J. Org. Chem., 6066 (1997) and TetrahedronLett., 6359 (1997) in the presence of a palladium catalyst underconditions similar to those described for the reaction of the haloderivative of formula (III) with the derivative of general formula (II).

[0061] When Ra and Rb represent hydrogen atoms, the amino derivativeobtained may be converted into a fluoro derivative by the action of analkaline nitrite (for example sodium nitrite) in acidic medium(tetrafluoroboric acid or hexafluorophosphoric acid) in water at atemperature of between −10° C. and 20° C., to prepare a diazoniumtetrafluoroborate or hexafluorophosphate, followed by pyrolysis of theproduct obtained according to the Baz-Schieman reaction, Org. Synth.,Coll 5, 133 (1973).

[0062] {circle over (5)} The heterocyclylalkylpiperidine derivatives ofgeneral formula (II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ representsan alkyloxy, alkylthio, cycloalkyloxy, cycloalkylthio, benzyloxy orheterocyclylmethyloxy radical, may be prepared by the action of thealcohol or of the corresponding thiol on the heterocyclylalkylpiperidinederivative for which one of the radicals R′_(i) is a bromine, iodine orchlorine atom. The reaction is generally carried out in an inert solventsuch as an ether (for example tetrahydrofuran or dioxane), an amide (forexample N,N-dimethylformamide) or dimethyl sulfoxide, in the presence ofan acid acceptor such as a trialkylamine (for example triethylamine), analkali metal hydride (for example sodium hydride), methyllithium orn-butyllithium, at a temperature of between 0° C. and the refluxtemperature of the reaction mixture.

[0063] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ represents a hydroxylradical may be prepared from the corresponding derivative for which oneof the radicals R′i is methoxy by the action of a strong acid such ashydrobromic acid, at a temperature of between 20° C. and the refluxtemperature of the reaction mixture.

[0064] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ represents atrifluoromethoxy radical may be obtained by analogy with the methoddescribed by Sun W. Y. Synlett., 11, 1279 (1997) to prepare a derivativefor which R′i is an —O—CS—SCH₃ radical, starting with the correspondinghydroxyl derivative; this radical is converted into a trifluoromethylradical by applying the methods described by Kuroboshi M. et al.,Tetrahedron Lett., 33(29), 4173 (1992) in the presence of1,3-dibromo-5,5-dimethylhydantoin in an HF-pyridine complex at atemperature of between 0° C. and 20° C.

[0065] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ represents an alkyloxy,cycloalkyloxy, phenoxy, benzyloxy, heterocyclyloxy orheterocyclylmethyloxy radical may be obtained by the action of thecorresponding halo derivative on the derivative of general formula (II)for which the R′i to be modified is hydroxyl. The process is optionallyperformed using the bromo derivative, in an inert solvent such as anether (for example tetrahydrofuran or dioxane), an amide (for exampleN,N-dimethylformamide) or dimethyl sulfoxide, in the presence of an acidacceptor such as a trialkylamine (for example triethylamine), an alkalimetal hydride (for example sodium hydride), methyllithium orN-butyllithium, optionally in the presence of a palladium salt (byanalogy with the methods described in J. Am. Chem. Soc., 4369 (1999);Tetrahedron Lett., 8005 (1997); Angew. Chem. Int. Ed. Engl., 2047(1998)), at a temperature of between 0° C. and the reflux temperature ofthe reaction mixture.

[0066] {circle over (6)} The heterocyclylalkylpiperidine derivatives ofgeneral formula (II) for which R₁ represents a trifluoromethyl radicalmay be prepared by the action of a trifluoromethylating agent(especially a bromo derivative Br—CF₃ or an iodo derivative I—CF₃) onthe heterocyclylalkylpiperidine derivative for which one of the radicalsR₁ is a bromine, iodine or chlorine atom, in the presence of copper or acopper(I) salt such as CuI, in a solvent such as dimethylformamide,between 20° C. and 150° C., by analogy with J.C.S. Chem. Commun., 1, 53(1992) or Chem. Commun., 18, 1389 (1993).

[0067] {circle over (7)} The heterocyclylalkylpiperidine derivatives ofgeneral formula (II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ representsan alkylthio, cycloalkylthio, trifluoromethylthio, phenylthio orheterocyclylthio radical may be obtained by the action of thecorresponding halo derivative on the heterocyclylalkylpiperidinederivative bearing a mercapto substituent. In one embodiment of thepresent invention, the process is performed using the bromo derivative,under the conditions described above for the action of a halo derivativeon an alcohol, at a temperature of between 20° C. and the refluxtemperature of the reaction mixture. In the case of thetrifluoromethylthio radical, the process is performed by analogy withthe method described in Tet. Lett., 33(44), 6677 (1992).

[0068] The mercapto derivative of the heterocyclyl-alkylpiperidine ofgeneral formula (II) may be obtained from theheterocyclylalkylpiperidine derivative for which one of the radicals R′iis a bromine, iodine or chlorine atom (in one embodiment of interest, abromine atom) by analogy with the methods described by Q. L. Zhou etal., Tetrahedron, 15, 4467 (1994); C. Bieniauz et al., TetrahedronLetters, 34, 6, 939 (1993) and E. D. Amstuts, J. Am. Chem. Soc., 68, 498(1946). The reaction is carried out, for example, in the presence ofNa₃PO₃S or Na₂S in an inert solvent such as an alcohol (for examplemethanol or ethanol), optionally in the presence of water, at atemperature of between 20° C. and the reflux temperature of the reactionmixture.

[0069] {circle over (8)} The heterocyclylalkylpiperidine derivatives ofgeneral formula (II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ representsa cyano radical may be obtained from the corresponding derivative forwhich one of the radicals. R′_(i) is a halogen atom, optionally abromine or iodine atom, by applying the methods described by Halley F.et al., Synth. Comm., 27(7), 1199 (1997) and Tschaen D. M. et al., J.Org. Chem., 60(14), 4324 (1995), in the presence of CuCN, or KCN andoptionally in the presence of a catalyst.

[0070] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ represents a carboxyl,alkyloxycarbonyl, cycloalkyloxycarbonyl or —CO—NRaRb radical may beprepared from the cyano derivative, according to the usual methods forconversion into an acid, an ester and an amide, which do not affect therest of the molecule, and some of the implementation conditions of whichhave been recalled above. In particular, in the presence of acarbodiimide (N,N′-dicyclohexylcarbodiimide) orN,N′-carbonyldiimidazole, in an ether (tetrahydrofuran or dioxane), anamide (N,N-dimethylformamide) or a chlorinated solvent (methylenechloride, 1,2-dichloroethane or chloroform), at a temperature of between0° C. and the reflux temperature of the reaction mixture.

[0071] {circle over (9)} The heterocyclylalkylpiperidine derivatives ofgeneral formula (II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ representsa hydroxymethyl radical may be obtained by reducing aheterocyclylalkylpiperidine derivative of general formula (II) for whichone of the radicals R′_(i) represents a carboxyl radical, using areducing agent such as, for example, lithium aluminum hydride or aborohydride, in an inert solvent such as an ether (for exampletetrahydrofuran or dioxane) or a chlorinated solvent (for examplemethylene chloride, 1,2-dichloroethane or chloroform), at a temperatureof between 0° C. and the reflux temperature of the reaction mixture.

[0072] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ represents analkyloxymethyl or cycloalkyloxymethyl radical may be obtained by theaction of the corresponding halo derivative (optionally the bromoderivative) on the corresponding heterocyclyl-alkylpiperidine derivativefor which the radical R′_(i) represents a hydroxymethyl radical. Thereaction is generally carried out in an inert solvent such as an ether(for example tetrahydrofuran or dioxane), an amide (for exampleN,N-dimethylformamide) or dimethyl sulfoxide, in the presence of an acidacceptor such as a trialkylamine (for example triethylamine) or analkali metal hydride (for example sodium hydride), at a temperature ofbetween 20° C. and 100° C.

[0073] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ represents a fluoromethylradical may be obtained by the action of a fluorinating agent on theheterocyclylalkylpiperidine derivative for which the correspondingradical R′_(i) represents a hydroxymethyl radical. The reaction may becarried out under the fluorinating conditions described above for theinstallation of a radical Re meaning fluorine.

[0074] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄ or R′₅ represents analkylthiomethyl or cycloalkylthiomethyl radical may be obtained by theaction of the corresponding thiol on a heterocyclylalkylpiperidinederivative for which the radical R′_(i) to be modified is halomethyl(wherein halogens according to one aspect of the invention are a bromineor a chlorine atom). The reaction is generally carried out in an inertsolvent such as an ether (for example tetrahydrofuran or dioxane), anamide (for example N,N-dimethylformamide) or dimethyl sulfoxide, in thepresence of an acid acceptor such as a trialkylamine (for exampletriethylamine) or an alkali metal hydride (for example sodium hydride),at a temperature of between 20° C. and the reflux temperature of thereaction mixture.

[0075] The heterocyclylalkylpiperidine derivatives bearing a halomethylradical R′_(i) are prepared from the corresponding derivative for whichR′_(i) is a hydroxymethyl radical by the action of a halogenating agent(halophosphorus derivative or thionyl chloride). The reaction isoptionally carried out in an inert solvent such as dichloromethane, at atemperature of between 0° C. and 60° C., optionally in the presence of abase such as pyridine.

[0076] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄, or R′₅ represents a radical—CH₂—NRaRb may be obtained by the action of an amine HNRaRb on aheterocyclylalkylpiperidine derivative for which the radical R′_(i) tobe modified is halomethyl (the halogen optionally being a bromine orchlorine atom). The reaction is carried out in an inert solvent such asan ether (for example tetrahydrofuran or dioxane), an amide (for exampleN,N-dimethylformamide) or dimethyl sulfoxide, in the presence of an acidacceptor such as a trialkylamine (for example triethylamine) or ahalkali metal hydride (for example sodium hydride), at a temperature ofbetween 20° C. and the reflux temperature of the reaction mixture. Thehalomethyl derivative is prepared as described above.

[0077] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄, or R′₅ represents a carboxymethylradical may be obtained by the action of an alkaline cyanide on aheterocyclylalkylpiperidine derivative for which the radical R′_(i) tobe modified is halomethyl (the halogen optionally being a bromine orchlorine atom), followed by hydrolysis of the nitrile. The reaction iscarried out using sodium cyanide or potassium cyanide in an organicsolvent such as dimethyl sulfoxide or dimethylformamide, or in awater-alcohol mixture, at a temperature of between 0° C. and the boilingpoint of the reaction mixture, followed by the action of a strong acidsuch as hydrochloric acid, optionally in the presence of a loweraliphatic alcohol, at a temperature of between 0° C. and the boilingpoint of the reaction mixture.

[0078] The heterocyclylalkylpiperidine derivatives of general formula(II) for which R₁, R′₁, R′₂, R′₃, R′₄, or R′₅ represents analkyloxycarbonylmethyl, cycloalkyloxy-carbonylmethyl or —CH₂—CO—NRaRbradical may be obtained from the corresponding acid according to theusual methods for converting an acid to an ester or amide which do notaffect the rest of the molecule, especially in the presence of acoupling agent such as a carbodiimide as described above.

[0079] The heterocyclic derivatives of general formula (III) for whichHal is a bromine atom, R₁ is defined as above, X₁ to X₄ represent,respectively, >C—R′_(i) to >C—R′₄ and X₅ represents >CH, may be preparedby brominating the corresponding 4-hydroxyquinolines using a brominatingagent such as phosphorus oxitribromide or thionyl bromide without asolvent, at a temperature of between 20° C. and 115° C.

[0080] The 4-hydroxyquinolines may be prepared by decarboxylating thecorresponding 3-carboxy-4-hydroxy-quinolines, working in a solvent suchas diphenyl ether at a temperature of between 100° C. and 260° C.

[0081] The 3-carboxy-4-hydroxyquinolines may be prepared by analogy withthe method described in European patent application EP-A-0 379 412,starting with the desired aniline derivative.

[0082] The heterocyclic derivatives of general formula (III) for whichHal is a bromine atom, R₁ is defined as above, X₁ to X₄ represent,respectively, >C—R′₁ to >C—R′₄ and X₅ represents >C—Cl, may be preparedby brominating the corresponding 3-chloro-4-hydroxyquinoline. Thebromination is generally carried out with triphenylphosphine dibromidein acetonitrile at a temperature of between 20° C. and 85° C.

[0083] The 3-chloro-4-hydroxyquinolines may be prepared by chlorinatinga 4-hydroxyquinoline. The chlorination is carried out, for example,using N-chlorosuccinimide in a solvent such as acetic acid, at atemperature of between 20° C. and 100° C.

[0084] The heterocyclic derivatives of general formula (III) for whichHal is a bromine atom, R₁ is defined as above, X₁ to X₄ represent,respectively, >C—R′₁ to >C—R′₄ and X₅ represents >C—COCF₃ may beprepared by analogy with the preparation of the derivatives for which X₅represents >CH, by brominating the corresponding4-hydroxy-3-fluoroacetylquinoline derivative. The reaction is carriedout without a solvent, using a brominating agent such as phosphorusoxytribromide, at a temperature of between 20° C. and 115° C. The4-hydroxy-3-trifluoroacetylquinoline may be prepared by analogy with themethod described for the preparation of 3-carboxy-4-hydroxyquinoline.

[0085] The heterocyclic derivatives of general formula (III) for whichHal is an iodine atom, R₁ is a methoxy radical, X₁ to X₄ represent,respectively, >C—R′₁ to >C—R′₄ and X₅ represents >C—F, may be preparedby analogy with the studies of E. Arzel et al., Tetrahedron, 55,12149-12156 (1999) starting with 3-fluoro-6-methoxyquinoline, by thesuccessive action of a base and then iodine. For example, lithiumdiisopropylamide in a solvent such as an ether (tetrahydrofuran) at atemperature of between −80° C. and 20° C. is used.

[0086] The 3-fluoro-6-methoxyquinoline may be obtained by pyrolysis of6-methoxyquinoline diazonium 3-tetra-fluoroborate or3-hexafluorophosphate according to the Balz-Schieman reaction, Org.Synth., Coll 5, 133 (1973), at a temperature of between 100° C. and 240°C. 6-Methoxyquinoline diazonium 3-tetrafluoroborate or6-methoxyquinoline diazonium 3-hexafluorophosphate may be obtained from3-amino-6-methoxyquinoline by the action of an alkaline nitrite (forexample sodium nitrite) in acidic medium (tetrafluoroboric acid orhexafluorophosphoric acid) in a solvent such as water at a temperatureof between −10° C. and +20° C., by analogy with the studies of A. Roe etal., J. Am. Chem. Soc., 71, 1785-86 (1949) or by the action of an alkylnitrite (such as, for example, isoamyl nitrite) and of thetrifluoroborate/diethyl ether complex in a solvent such as an ether (forexample tetrahydrofuran) at a temperature of between −10° C. and +10° C.

[0087] 3-Amino-6-methoxyquinoline is prepared as described by N.Heindel, J. Med. Chem. 13, 760 (1970).

[0088] The heterocyclic derivatives of general formula (III) for whichHal is a bromine atom, R₁ is defined as above, X₂ to X₄ represent,respectively, >C—R′₂ to >C—R′₄ and X₁ represents a nitrogen atom oralternatively X₁, X₃, and X₄ represent, respectively, >C—R′₁, >C—R′₃,and >C—R′₄ and X₂ represents a nitrogen atom, and X₅ represents >CHor >C—Cl, may be prepared by analogy with the methods described abovewhen X₁ to X₄ represent, respectively, >C—R′₁ to >C—R′₄ or according tothe syntheses described by Adams J. T. et al., J. Am. Chem. Soc., 68,1317 (1946) for the 1,5-naphthyridines and S. Radl et al., Collect.Czech. Chem. Commun., 56, 2420 (1991) for the 1,7-naphthyridines,starting with 3-aminopyridines.

[0089] The hydroxynaphthyridine required to carry out the reaction isalso prepared by analogy with the methods described above for thehydroxyquinolines, but starting with 3-aminopyridine or its substitutedderivatives. The 3-aminopyridine derivatives may be obtained byadaptation of the methods described in “The Chemistry of HeterocyclicCompounds”, Vol. 14, Pyridine and its Derivatives, Supplement Part III,page 41. Ed. R. A. Abramovitch, InterScience Publication.

[0090] The heterocyclic derivatives of general formula (III) for whichHal is a bromine atom, R₁ is defined as above, X₁, X₂, and X₄ represent,respectively, >C—R′₁, >C—R′₂, and >C—R′₄, X₃ represents a nitrogen atomand X₅ represents >CH or >C—Cl, may be prepared by analogy with themethods described above when X₁ to X₄ represent respectively, >C—R′₁ to>C—R′₄ or according to the syntheses described by D. Heber et al.,Arzneim-Forsch, 44, 809 (1994) starting with 2-aminopyridines orsubstituted derivatives thereof.

[0091] The 2-aminopyridines may be obtained by applying or adapting themethods described in “The Chemistry of Heterocyclic Compounds”, Vol. 14,Pyridine and its Derivatives, Supplement Part III, page 41, Ed. R. A.Abramovitch, Interscience Publication.

[0092] The derivatives of general formula (III) for which Hal is abromine atom, R₁ is defined as above and X₅ represents a nitrogen atommay be obtained from 2-amino-benzenamides as described in J. Am. Chem.Soc., 69, 184 (1947). 2-Amino-benzenamide is cyclized in the presence ofan alkyl orthoformate such as ethyl orthoformate in a solvent such asdiethylene glycol at a temperature of between 105° C. and 120° C. togive 4-hydroxyquinazoline, which is brominated as described above. The2-aminobenzenamide is obtained from the corresponding aniline byapplying or adapting the methods described by V. Snieckus, Chem. Rev.,90, 879 (1990) and Pure Appl. Chem., 62, 2047 (1990).

[0093] The heterocyclic derivatives of general formula (III) for whichHal is a bromine atom, R₁ is defined as above and X₄ is a nitrogen atommay be obtained from 2-acetylaniline as described in Synth. Commun., 19,3087 (1989). The 4-hydroxycinnoline obtained is brominated under theconditions described above. The 2-acetylanilines are obtained from thecorresponding aniline by applying the methods cited above for2-aminobenzenamide.

[0094] The piperidine derivatives of general formula (IV) for which n=0and R″₂ represents-carboxyl may be prepared from the correspondingpiperidine derivative of general formula:

[0095] in which R″₂ defined as above is protected beforehand and Rz isdefined as above, by analogy with the studies of Koppel, J. Chem. Soc.Chem. Commun., 473 (1975) by reaction between the piperidine derivativeand vinyl phenyl sulfoxide in the presence of a base (for example sodiumhydride, lithium diisopropylamide or lithium hexamethyldisyliylamide) ina solvent such as an ether (for example tetrahydrofuran) at atemperature of between 0° C. and 100° C. The intermediate adductobtained is then thermolyzed at between 60° C. and 150° C. in an inertsolvent (for example chloroform, tetrahydrofuran, toluene or xylene). Rzis advantageously a protecting group for the nitrogen atom such as, forexample, t-butyloxycarbonyl.

[0096] The piperidine derivatives of general formula (IV) for which n=1or 2 and R″₂ represents carboxyl may be prepared from the correspondingpiperidine derivative of general formula (V) for which R″₂ is protectedbeforehand, according to or by analogy with the methods described belowin the examples. In particular, the process is performed by thesuccessive action of a base such as, for example, lithiumdiisopropylamide or n-butyllithium, in a solvent such as an ether (forexample tetrahydrofuran) at a temperature of between −80° C. and 0° C.,and then of an alkenyl halide (allyl halide or 1-halo-3-butene).

[0097] The piperidine derivatives of general formula (IV) for which n isdefined as above and R″₂ is alkyloxycarbonyl, cycloalkyloxycarbonyl,—CO—NRaRb, alkyloxycarbonylmethyl, alkyloxycarbonylethyl,cycloalkyloxycarbonylmethyl, cycloalkyloxycarbonylethyl, —CH₂—CONRaRb,or —(CH₂)₂—CONRaRb or for which Rc in R₂ represents alkyloxycarbonyl,cycloalkyloxycarbonyl or —CO—NRaRb may be prepared from thecorresponding carboxylic acid derivative, according to the usual methodsfor converting into ester or amide which do not affect the rest of themolecule. The esters are prepared in the presence of a coupling agentsuch as a carbodiimide (for example (N,N′-dicyclocarbodiimide) orN,N′-carbonyldiimidazole in an ether (for example tetrahydrofuran ordioxane), an amide (for example dimethylformamide) or a chlorinatedsolvent (for example dichloromethane, 1,2-dichloroethane or chloroform),at a temperature of between 0° C. and the reflux temperature of thereaction mixture. The amides are prepared by the action of thecorresponding amine under conditions identical to those described above.In particular also, when it involves the preparation of a derivative forwhich Rc in R″2 is an ester, by analogy with the methods described bySaha et al., J. Chem. Soc. Perkin I, 505 (1985), by the action of adiazoalkane (for example diazomethane) in an ether (for example diethylether) at a temperature of between −10° C. and 5° C.

[0098] The piperidine derivatives of general formula (IV) for which n isdefined as above and R″₂ represents cyano, —CH₂—CN, or —(CH₂)₂—CN may beprepared from the corresponding amides by the action of a dehydratingagent, by adapting the method described by Bieron et al., Zabicky ”TheChemistry of Amides,” Wiley, pp. 274-283 (1970). The reaction is carriedout in the presence of phosphorus pentoxide or phosphorus oxychloridewith or without solvent, at a temperature of between 20° C. and thereflux temperature of the reaction mixture.

[0099] The piperidine derivatives of general formula (IV) for which n isdefined as above and R″₂ represents hydroxymethyl, cyanomethyl orcarboxymethyl may be prepared from the piperidine derivative of generalformula:

[0100] in which Rz and n are defined as above, and Ry represents areadily hydrolyzable protecting radical, in particular, by the action ofa hydride (for example lithium aluminum hydride or diisobutylaluminumhydride) in a solvent such as an ether (for example tetrahydrofuran) ata temperature of between 20° C. and 60° C. to prepare the piperidinederivative for which R″₂ is hydroxymethyl, followed by converting thehydroxymethyl radical into a cyanomethyl radical and then acarboxymethyl radical according to the usual methods which do not affectthe rest of the molecule.

[0101] When Ry represents a readily hydrolyzable radical, it may bechosen especially from alkyl (1 to 4 carbon atoms in a straight orbranched chain), benzyl, cycloalkyl, phenylpropyl, and allyl.

[0102] The conversion into acid may be carried out in particular fromthe latter compound, by the action of a halogenating agent such as, forexample, thionylchloride or phosphorus trichloride or tribromide or bythe action of an alkanesulfonyl chloride (for example methanesulfonylchloride or p-toluenesulfonyl chloride) in an inert solvent (for exampledichloromethane), followed by the action of an alkaline cyanide (forexample potassium cyanide or sodium cyanide) and hydrolysis. Thehalogenation reaction is carried out in a chlorinated solvent (forexample dichloromethane or chloroform), at a temperature of between 0°C. and the reflux temperature of the reaction mixture. The reaction ofthe alkaline cyanide may be carried out in dimethyl sulfoxide, an amide(for example dimethylformamide), a ketone (for example acetone), anether (for example tetrahydrofuran) or an alcohol (for example methanolor ethanol), at a temperature of between 20° C. and the refluxtemperature of the reaction mixture. The nitrile is hydrolyzed accordingto the conventional methods which do not affect the rest of themolecule, especially by the action of hydrochloric acid in methanolicmedium, at a temperature of between 20° C. and 70° C., followed bysaponification of the ester obtained (for example with sodium hydroxidein a mixture of dioxane and water), or directly by the action of aqueoussulfuric acid at a temperature of between 50° C. and 80° C.

[0103] The piperidine derivatives of general formula (IV) for which nand Rz are defined as above and R″₂ represents a 2-carboxyethyl radicalmay be prepared from the derivative of general formula (IV) for whichR″₂ represents a hydroxymethyl radical via the halo derivative (preparedas described above) and then coupling with the sodium salt of diethylmalonate followed by acidic hydrolysis in aqueous medium of the productobtained.

[0104] The piperidine derivatives of general formula (IV) for which nand Rz are defined as above and R″₂ represents carboxyhydroxymethyl orcarboxycarbonyl may be prepared by homologation of the piperidinederivative of general formula:

[0105] in which Rz and n are defined as above, by applying or adaptingthe methods described by M. Mizuno et al., Tetrahedron Lett. 39, 9209(1998). The reaction is carried out by the action of a dialkylphosphorocyanidate (for example diethyl phosphorocyanidate) in thepresence of an organic base (for example triethylamine) in an ether (forexample tetrahydrofuran) at a temperature of between −50° C. and 10° C.The intermediate dicyanophosphate obtained is then hydrolyzed in acidicmedium (for example concentrated hydrochloric acid) in a polar solvent(for example water) at the reflux temperature of the reaction mixture.The derivatives for which R″₂ is carboxycarbonyl are obtained byoxidation of the corresponding ester, by adapting the methods describedby Burhardt et al., Tetrahedron Lett., 29, 3433 (1988) followed byhydrolysis of the product obtained. In particular by the action of anoxidizing agent such as triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)onein a solvent such as a nitrile or a chlorinated derivative (for exampleacetonitrile or dichloromethane) at a temperature of between 0° C. and40° C., followed by hydrolysis by the action of a base (for examplesodium hydroxide) in an aqueous-alcoholic solvent (for examplewater-methanol) at a temperature of between 20° C. and the refluxtemperature of the reaction mixture.

[0106] The piperidine derivatives of general formula (IV) for which nand Rz are defined as above and R″₂ represents —CF₂-Rc may be preparedby the action of a fluorinating agent on a piperidine derivative ofgeneral formula (IV) for which R″₂ is a radical —CO-Rc, Rc being anester, by analogy with the methods described by M. Parisi et al., J.Org. Chem., 60, 5174 (1995), optionally followed by hydrolysis of theester if it is desired to obtain a piperidine derivative for which Rc iscarboxyl. The fluorinating conditions are similar to those describedabove for the preparation of derivatives for which Re in Y is a fluorineatom. The hydrolysis is carried out by the action of a base in anaqueous-alcoholic solvent under the conditions described above.

[0107] The piperidine derivatives of general formula (IV) for which nand Rz are defined as above and R″₂ represents a radical —CH═CH-Rc maybe prepared by oxidation to aldehyde of the derivative of generalformula (IV) for which R″₂ represents a hydroxymethyl radical byadapting the methods described in Org. Synth. Coll., Vol. II, p. 541,Coll. Vol. 5, p. 242, followed by conversion to a derivative for whichR″₂ is —CH═CH-Rc in which Rc is an ester, by applying the Wittig methodoptionally followed by hydrolysis of the ester obtained to an acid. Theoxidation is carried out by the action of an oxidizing agent (forexample potassium dichromate) in acidic medium (for example sulfuricacid) in a polar solvent (for example water) or chromium oxide in thepresence of a base (for example pyridine) in a chlorinated solvent (forexample dichloromethane) at a temperature of between 0° C. and 20° C.The conversion to an unsaturated derivative is carried out by adaptingthe methods described by Johnson in “Ylid Chemistry,” Academic Press(1966) by the action of a phosphorus ylid (for examplecarbethoxymethylene-triphenylphosphorane) in a hydrocarbon (for exampletoluene) at a temperature of between 60° C. and the reflux temperatureof the reaction mixture. The hydrolysis is carried out according to themethods described above.

[0108] The piperidine derivatives of general formula (IV) for which nand Rz are defined as above and R′₂ represents a radical C(CH₃)₂Rc or—C(cycloalk)Rc may be prepared from a derivative of general formula (IV)for which R″₂ is an ester of the acid for which R″₂ is —CH₂COOH byadapting the methods described by Ashutosh et al., Tetrahedron Lett.,40, 4733 (1999) and Sauers, J. Org. Chem., 57, 671 (1992) optionallyfollowed by hydrolysis of the ester obtained. The reaction is carriedout in particular by the successive action of an amide (for examplelithium diisopropylamide) followed by a methyl halide (for examplemethyl iodide) or a derivative of formula Hal-Alk-Hal (Hal in oneembodiment being a bromine atom) in a polar solvent (for examplehexamethylphosphorotriamide) at a temperature of between 0° C. and 60°C.

[0109] It is understood that the processes listed above for thepreparation of the piperidine derivatives of general formula (IV) mayalso be applied to the derivatives of general formula (II) if optionallyfirst one couples the piperidine with the heterocyclic derivative ofgeneral formula (III) and then converts the radical R₂ under theconditions described above.

[0110] It is also understood that the methods described below in theexamples also form part of the present invention.

[0111] It is understood that the derivatives of general formulae (I) and(II) may exist in enantiomeric or diastereoisomeric forms or in syn oranti form. The enantiomeric or diastereoisomeric and syn or anti formsand the mixtures thereof also fall within the context of the presentinvention. These forms may be separated according to the usual methods,especially by chromatography on silica or by high performance liquidchromatography (HPLC).

[0112] The heterocyclylalkylpiperidine derivatives of general formula(I) may be purified, where appropriate, by physical methods such ascrystallization or chromatography.

[0113] The heterocyclylalkylpiperidine derivatives of general formula(I) may, where appropriate, be converted into addition salts with acids,by the known methods. It is understood that these salts also fall withinthe context of the present invention.

[0114] As examples of addition salts with pharmaceutically acceptableacids, mention may be made of the salts formed with mineral acids(hydrochlorides, hydrobromides, sulfates, nitrates and phosphates) orwith organic acids (succinates, fumarates, tartrates, acetates,propionates, maleates, citrates, methanesulfonates, ethanesulfonates,phenylsulfonates, p-toluenesulfonates, isethionates, naphthylsulfonatesor camphorsulfonates, or with substitution derivatives of thesecompounds).

[0115] Some of the heterocyclylalkylpiperidine derivatives of generalformula (I) bearing a carboxyl radical may be converted into metal saltsor into addition salts with nitrogen bases according to the methods thatare known per se. These salts also fall within the context of thepresent invention. The salts may be obtained by the action of a metallicbase (for example an alkali metal or alkaline-earth metal), ammonia oran amine, on a product according to the invention, in a suitable solventsuch as an alcohol, an ether or water, or by exchange reaction with asalt of an organic acid. The salt formed precipitates after optionalconcentration of the solution, and is separated out by filtration,settling or freeze-drying.

[0116] Examples of pharmaceutically acceptable salts which may bementioned are the salts with alkali metals (sodium, potassium orlithium) or with alkaline-earth metals (magnesium or calcium), theammonium salts or the salts of nitrogen bases (ethanolamine,diethanolamine, trimethylamine, triethylamine, methylamine, propylamine,diisopropylamine, N-N-dimethylethanolamine, benzylamine,dicyclohexylamine, N-benzyl-β-phenethylamine,N,N′-dibenzylethylenediamine, diphenylenediamine, benzhydrylamine,quinine, choline, arginine, lysine, leucine or dibenzylamine).

[0117] The heterocyclylalkylpiperidine derivatives according to theinvention are particularly advantageous antibacterial agents.

[0118] In vitro, the heterocyclylalkylpiperidine derivatives accordingto the invention have been found to be active on gram-positivemicroorganisms at concentrations of between 0.03 μg/ml and 4 μg/ml onmeticillin-resistant Staphylococcus aureus AS5155, and also, for most ofthem, at concentrations of between 0.03 μg/ml and 8 μg/ml onStreptococcus pneumoniae 6254-01; they have also been found to be activeon gram-negative microorganisms such as, for example, and in anonlimiting manner, on Moraxella catarrhalis IPA 152, at concentrationsof between 0.12 μg/ml and 64 μg/ml. In vivo, they have been found to beactive on experimental infections of mice with Staphylococcus aureusIP8203, either subcutaneously at doses of between 18 mg/kg and 150 mg/kg(DC₅₀), or orally at doses of between 20 mg/kg and 150 mg/kg.

[0119] Finally, the products according to the invention are particularlyadvantageous on account of their low toxicity. None of the products hasshown any toxicity subcutaneously at the dose of 100 mg/kg in mice (twoadministrations).

[0120] In the general formula (I), the products for which

[0121] X₁, X₂, X₃, X₄ and X₅ represent, respectively, >C—R′₁ to >C—R′₅,or alternatively not more than one of them represents a nitrogen atom,

[0122] R₁, R′₁, R′₂, R′₃, R′₄ and R′₅ are identical or different andrepresent a hydrogen or halogen atom or an alkyl or alkyloxy radical, orrepresent a methylene radical substituted with alkyloxy,

[0123] R₂ represents carboxyl, alkyloxycarbonyl or —CONRaRb (for whichRa represents a hydrogen atom and Rb represents a hydrogen atom or ahydroxyl radical) or

[0124] R₂ represents hydroxymethyl, alkyl containing 1 or 2 carbon atomssubstituted with carboxyl or alkyloxy-carbonyl,

[0125] R₃ represents a radical alk-R°3 for which alk is an alkyl radicaland R°₃ represents hydrogen, cycloalkyl, cycloalkylthio, phenyl,phenoxy, phenylthio, phenylamino, heterocyclyloxy or heterocyclylthio oralternatively R°3 represents —CR′b=CR′c-R′a for which R′a representsphenyl, and for which R′b and R′c represent hydrogen,

[0126] Y represents a radical >CH—Re for which Re is hydrogen, fluoro orhydroxyl,

[0127] n is an integer from 2 to 3,

[0128] it being understood that the phenyl or heterocyclyl radicals orportions mentioned above may be optionally substituted on the ring with1 to 4 halogens.

[0129] Of special interest are the heterocyclylalkyl piperidinederivatives of general formula (I) mentioned below:

[0130]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0131]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0132]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiazol-2-thioethyl)piperidine-4-carboxylicacid

[0133]1-(2-Cyclopentylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[0134]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylicacid

[0135] and also the salts thereof.

[0136] Among the products according to the invention that may bementioned are the heterocyclylalkylpiperidine derivatives of generalformula (I), the names of which follow:

[0137]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylicacid

[0138]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-carboxylicacid

[0139]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0140]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0141]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0142]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-carboxylicacid

[0143]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0144]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0145]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0146]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0147]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0148]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0149]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0150]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0151]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthiopropyl]piperidine-4-carboxylicacid

[0152]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0153]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0154]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0155]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0156]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0157]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]-piperidine-4-carboxylicacid

[0158]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0159]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0160]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0161]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0162]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]-piperidine-4-carboxylicacid

[0163]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]-piperidine-4-carboxylicacid

[0164]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]-piperidine-4-carboxylicacid

[0165]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0166]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0167]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0168]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0169]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]-piperidine-4-carboxylicacid

[0170]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0171]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0172]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0173]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0174]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0175]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0176]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0177]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]-piperidine-4-carboxylicacid

[0178]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0179]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]-piperidine-4-carboxylicacid

[0180]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0181]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]-piperidine-4-carboxylicacid

[0182]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]-piperidine-4-carboxylicacid

[0183]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]-piperidine-4-carboxylicacid

[0184]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]-piperidine-4-carboxylicacid

[0185]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]-piperidine-4-carboxylicacid

[0186]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]-piperidine-4-carboxylicacid

[0187]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]-piperidine-4-carboxylicacid

[0188]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]-piperidine-4-carboxylicacid

[0189]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]-piperidine-4-carboxylicacid

[0190]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]-piperidine-4-carboxylicacid

[0191]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]-piperidine-4-carboxylicacid

[0192]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-carboxylicacid

[0193]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]-piperidine-4-carboxylicacid

[0194]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-carboxylicacid

[0195]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-carboxylicacid

[0196]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0197]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-carboxylicacid

[0198]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-carboxylicacid

[0199]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-carboxylicacid

[0200]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0201]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-carboxylicacid

[0202]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-carboxylicacid

[0203]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-carboxylicacid

[0204]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-carboxylicacid

[0205]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-carboxylicacid

[0206]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperidine-4-carboxylicacid

[0207]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-carboxylicacid

[0208]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-carboxylicacid

[0209]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperidine-4-carboxylicacid

[0210]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0211]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-carboxylicacid

[0212]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-carboxylicacid

[0213]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-carboxylicacid

[0214]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-carboxylicacid

[0215]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-carboxylicacid

[0216]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-carboxylicacid

[0217]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-carboxylicacid

[0218]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-carboxylicacid

[0219]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-carboxylicacid

[0220]4-(3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-carboxylicacid

[0221]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-carboxylicacid

[0222]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-(pyrazin-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0223]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0224]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0225]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0226]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0227]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0228]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0229]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0230]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0231]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0232]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0233]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0234]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0235]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0236]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0237]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0238]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0239]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0240]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0241]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0242]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0243]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0244]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0245]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0246]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0247]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0248]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0249]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-carboxylicacid

[0250]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]-piperidine-4-carboxylicacid

[0251]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0252]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0253]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0254]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0255]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0256]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0257]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0258]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0259]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0260]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0261]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0262]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0263]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0264]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0265]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0266]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0267]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0268]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0269]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylic acid

[0270]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0271]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0272]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0273]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0274]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0275]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0276]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0277]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0278]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0279]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0280]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0281]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0282]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0283]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0284]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0285] 4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio) ethyl]piperidine-4-carboxylicacid

[0286]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0287]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0288]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0289]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0290]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0291]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0292]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0293]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0294]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0295]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0296]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0297]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0298]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0299]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0300]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0301]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0302]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0303]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0304]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0305]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0306]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0307]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0308]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0309]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0310]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0311]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0312]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0313]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0314]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0315]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0316]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0317]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0318]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0319]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0320]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0321]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0322] 4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy) ethyl]piperidine-4-carboxylic acid

[0323]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0324]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0325]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0326]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0327]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0328]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0329]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0330]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0331]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0332]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0333]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0334]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0335]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0336]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0337]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0338]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0339]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0340]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0341]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0342]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0343]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0344]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0345]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]-piperidine-4-carboxylicacid

[0346]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]-piperidine-4-carboxylicacid

[0347]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]-piperidine-4-carboxylicacid

[0348]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0349]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0350]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-carboxylicacid

[0351]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-carboxylicacid

[0352]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-carboxylicacid

[0353]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-carboxylicacid

[0354]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]-piperidine-4-carboxylicacid

[0355]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-carboxylicacid

[0356]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-carboxylicacid

[0357]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-carboxylicacid

[0358]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0359]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0360]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0361]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0362]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0363]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0364]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0365]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-carboxylicacid

[0366]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-carboxylicacid

[0367]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0368]4-(3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0369]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0370]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0371]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0372]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]-piperidine-4-carboxylicacid

[0373]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperidine-4-carboxylicacid

[0374] 4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-carboxylicacid

[0375]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-carboxylicacid

[0376]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-carboxylicacid

[0377]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0378] 4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0379]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0380]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0381]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0382]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0383]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0384]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0385]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0386]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0387]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0388]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0389]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-carboxylicacid

[0390]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-carboxylicacid

[0391]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-carboxylicacid

[0392]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-carboxylicacid

[0393]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0394]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0395]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-carboxylicacid

[0396]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0397]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-prop-2-ynyl]piperidine-4-carboxylicacid

[0398]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-prop-2-ynyl]piperidine-4-carboxylicacid

[0399] 4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylicacid

[0400]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-carboxylicacid

[0401]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0402]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0403]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0404]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0405]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-carboxylicacid

[0406]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0407]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0408]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0409]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0410]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0411]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0412]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthio-propyl]piperidine-4-carboxylicacid

[0413]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0414]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0415]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0416]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0417]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0418]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperidine-4-carboxylicacid

[0419]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0420]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0421]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0422]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0423]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0424]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0425]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0426]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0427]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0428]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0429]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0430]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0431]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperidine-4-carboxylicacid

[0432]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0433]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0434]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0435]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0436]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0437]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0438]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0439]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperidine-4-carboxylicacid

[0440]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0441]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperidine-4-carboxylicacid

[0442]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0443]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperidine-4-carboxylicacid

[0444]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]piperidine-4-carboxylicacid

[0445]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]piperidine-4-carboxylicacid

[0446]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]piperidine-4-carboxylicacid

[0447]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]piperidine-4-carboxylicacid

[0448]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]piperidine-4-carboxylicacid

[0449]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]piperidine-4-carboxylicacid

[0450]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperidine-4-carboxylicacid

[0451]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperidine-4-carboxylicacid

[0452]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperidine-4-carboxylicacid

[0453]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperidine-4-carboxylicacid

[0454]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-carboxylicacid

[0455]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperidine-4-carboxylicacid

[0456]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-carboxylicacid

[0457]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-carboxylicacid

[0458]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0459]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0460]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-carboxylicacid

[0461]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-carboxylicacid

[0462]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0463]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-carboxylicacid

[0464]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0465]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-carboxylicacid

[0466]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-carboxylicacid

[0467]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0468]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-carboxylicacid

[0469]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-carboxylicacid

[0470]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-carboxylicacid

[0471]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperidine-4-carboxylicacid

[0472]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-carboxylicacid

[0473]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-carboxylicacid

[0474]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperidine-4-carboxylicacid

[0475]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0476]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-carboxylicacid

[0477]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-carboxylicacid

[0478]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-carboxylicacid

[0479]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-carboxylicacid

[0480]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-carboxylicacid

[0481]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-carboxylicacid

[0482]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-carboxylicacid

[0483]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-carboxylicacid

[0484]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-carboxylicacid

[0485]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-carboxylicacid

[0486]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-carboxylicacid

[0487]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0488]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0489]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0490] 4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0491]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0492]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0493]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0494]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0495]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0496]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0497]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0498]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0499]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0500]4-(3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0501]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0502]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0503]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0504]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0505]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0506]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0507]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0508]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0509]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0510]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0511]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0512]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0513]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0514]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0515]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0516]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0517]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0518]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0519]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid.

[0520]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0521] 4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylic acid

[0522]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0523]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0524]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0525]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0526]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0527]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0528]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0529]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0530]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0531]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylic acid

[0532]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0533]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0534]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0535]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0536]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0537]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0538]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0539]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0540]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0541]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0542]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0543]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0544]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0545]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0546]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0547]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0548]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0549]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0550]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0551]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0552]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0553]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0554]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0555]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0556]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0557]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0558]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0559]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0560]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0561]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0562]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0563]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0564]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0565]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0566]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0567]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0568]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0569]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0570]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0571]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0572]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0573] 4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0574]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0575]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0576]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0577]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0578]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0579]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0580]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0581]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0582]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0583]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0584]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0585]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0586]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0587]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0588]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0589]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0590]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0591]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0592]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0593]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0594]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0595]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0596]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0597]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0598]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0599]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0600]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0601]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0602] 4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0603]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0604]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0605]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0606]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0607]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0608]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0609]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0610]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0611]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0612]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0613]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0614]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0615]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0616]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0617]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0618]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0619]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0620]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0621]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0622]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0623]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0624]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0625]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0626]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0627]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0628]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0629]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0630]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0631]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0632]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0633]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0634]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0635]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0636]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0637]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0638]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0639]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0640]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0641]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0642]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0643]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0644]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0645]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0646]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0647]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0648]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0649]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0650]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0651]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0652]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0653]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0654]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0655]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0656]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0657]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0658]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0659]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0660]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0661]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0662]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0663]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0664]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0665]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0666]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0667]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0668]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylicacid

[0669]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-carboxylicacid

[0670]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0671]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0672]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0673]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperidine-4-carboxylicacid

[0674]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-carboxylicacid

[0675]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0676]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0677]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0678]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0679]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-carboxylicacid

[0680]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0681]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0682]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0683]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthio-propyl]piperidine-4-carboxylicacid

[0684]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0685]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0686]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0687]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-carboxylicacid

[0688]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0689]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperidine-4-carboxylicacid

[0690]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0691]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0692]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0693]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0694]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0695]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0696]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0697]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0698]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0699]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0700]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0701]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperidine-4-carboxylicacid

[0702]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0703]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0704]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0705]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0706]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-carboxylicacid

[0707]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-carboxylicacid

[0708]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0709]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperidine-4-carboxylicacid

[0710]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0711]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperidine-4-carboxylicacid

[0712]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-carboxylicacid

[0713]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperidine-4-carboxylicacid

[0714]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]piperidine-4-carboxylicacid

[0715]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]piperidine-4-carboxylicacid

[0716]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]piperidine-4-carboxylicacid

[0717]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]piperidine-4-carboxylicacid

[0718]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]piperidine-4-carboxylicacid

[0719]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]piperidine-4-carboxylicacid

[0720]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperidine-4-carboxylicacid

[0721]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperidine-4-carboxylicacid

[0722]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperidine-4-carboxylicacid

[0723]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperidine-4-carboxylicacid

[0724]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-carboxylicacid

[0725]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperidine-4-carboxylicacid

[0726]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-carboxylicacid

[0727]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-carboxylicacid

[0728]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0729]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0730]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-carboxylicacid

[0731]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-carboxylicacid

[0732]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0733]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-carboxylicacid

[0734]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0735]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-carboxylicacid

[0736]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-carboxylicacid

[0737]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0738]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-carboxylicacid

[0739]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-carboxylicacid

[0740]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-carboxylicacid

[0741]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperidine-4-carboxylicacid

[0742]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-carboxylicacid

[0743]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-carboxylicacid

[0744]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperidine-4-carboxylicacid

[0745]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0746]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-carboxylicacid

[0747]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-carboxylicacid

[0748]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-carboxylicacid

[0749]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-carboxylicacid

[0750]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-carboxylicacid

[0751]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-carboxylicacid

[0752]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-carboxylicacid

[0753]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-carboxylicacid

[0754]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-carboxylicacid

[0755]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-carboxylicacid

[0756]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-carboxylicacid

[0757]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-carboxylicacid

[0758]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0759]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0760]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0761]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0762]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0763]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0764]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0765]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0766]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0767]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0768]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0769]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0770]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0771]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0772]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0773]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0774]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0775]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0776]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0777]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0778]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0779]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0780]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0781]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0782]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0783]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0784]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0785]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0786]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0787]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0788]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0789]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0790]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0791]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0792]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0793]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0794]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0795]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0796]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0797]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0798]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0799]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0800]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0801]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0802]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0803]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0804]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0805]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0806]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0807]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0808]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0809]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0810]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0811]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0812]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0813]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0814]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0815]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0816]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0817]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0818]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0819]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0820]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0821]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0822]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0823]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0824]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0825]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0826]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0827]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0828]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0829]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0830] 4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0831]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0832]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0833]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0834]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0835]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0836]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0837]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0838]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0839]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0840]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0841]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0842]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0843]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0844]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0845]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0846]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0847]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0848]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0849]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0850]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0851]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0852]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0853]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0854]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0855]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0856]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0857]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-carboxylicacid

[0858]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-carboxylicacid

[0859]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0860]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0861]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0862]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0863]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0864]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0865]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid

[0866]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid

[0867]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[0868]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0869]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-carboxylicacid

[0870]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0871]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0872]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0873]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0874]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0875]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0876]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0877]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0878]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0879]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0880]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0881]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0882]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0883]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0884]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0885]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0886]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0887]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0888]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0889]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0890]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0891]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0892]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0893]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0894]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0895]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0896]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0897]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0898]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0899]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0900]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0901]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0902]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0903]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0904]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0905]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0906]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0907]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0908]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0909]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0910]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0911]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0912]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0913]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0914]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0915]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0916]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0917]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0918]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0919]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0920]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0921]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0922]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0923]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0924]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0925]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0926]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0927]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0928]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0929]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0930]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0931]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxylicacid

[0932]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0933]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-carboxylicacid

[0934]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0935]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-carboxylicacid

[0936]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0937]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[0938]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0939]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxylicacid

[0940]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-aceticacid

[0941]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-aceticacid

[0942]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[0943]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-aceticacid

[0944]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-aceticacid

[0945]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperidine-4-aceticacid

[0946]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-aceticacid

[0947]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperidine-4-aceticacid

[0948]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-aceticacid

[0949]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperidine-4-aceticacid

[0950]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-aceticacid

[0951]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-aceticacid

[0952]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[0953]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[0954]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[0955]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthiopropyl]piperidine-4-aceticacid

[0956]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-aceticacid

[0957]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-aceticacid

[0958]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-aceticacid

[0959]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-aceticacid

[0960]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)-ethyl]piperidine-4-aceticacid

[0961]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)-propyl]piperidine-4-aceticacid

[0962]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)-ethyl]piperidine-4-aceticacid

[0963]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[0964]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[0965]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[0966]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[0967]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[0968]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[0969]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[0970]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-aceticacid

[0971]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[0972]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[0973]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[0974]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)-propyl]piperidine-4-aceticacid

[0975]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-aceticacid

[0976]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-aceticacid

[0977]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-aceticacid

[0978]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-aceticacid

[0979]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-aceticacid

[0980]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-aceticacid

[0981]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-aceticacid

[0982]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)-propyl]piperidine-4-aceticacid

[0983]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-aceticacid

[0984]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)-propyl]piperidine-4-aceticacid

[0985]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-aceticacid

[0986]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)-propyl]piperidine-4-aceticacid

[0987]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)-ethyl]piperidine-4-aceticacid

[0988]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)-propyl]piperidine-4-aceticacid

[0989]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)-ethyl]piperidine-4-aceticacid

[0990]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)-propyl]piperidine-4-aceticacid

[0991]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)-ethyl]piperidine-4-aceticacid

[0992]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)-propyl]piperidine-4-aceticacid

[0993]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)-ethyl]piperidine-4-aceticacid

[0994]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)-propyl]piperidine-4-aceticacid

[0995]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)-ethyl]piperidine-4-aceticacid

[0996]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)-propyl]piperidine-4-aceticacid

[0997]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)-ethyl]piperidine-4-aceticacid

[0998]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)-propyl]piperidine-4-aceticacid

[0999]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-aceticacid

[1000]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-aceticacid

[1001]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1002]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1003]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-aceticacid

[1004]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-aceticacid

[1005]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1006]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-aceticacid

[1007]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-aceticacid

[1008]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-aceticacid

[1009]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-aceticacid

[1010]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-aceticacid

[1011]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-aceticacid

[1012]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-aceticacid

[1013]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperidine-4-aceticacid

[1014]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-aceticacid

[1015]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-aceticacid

[1016]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperidine-4-aceticacid

[1017]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-aceticacid

[1018]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-aceticacid

[1019]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-aceticacid

[1020]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-aceticacid

[1021]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-aceticacid

[1022]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-aceticacid

[1023]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-aceticacid

[1024]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-aceticacid

[1025]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-aceticacid

[1026]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-aceticacid

[1027]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-aceticacid

[1028]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-aceticacid

[1029]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-aceticacid

[1030]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1031]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1032]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1033]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1034]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1035]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1036]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1037]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1038]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1039]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1040]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1041]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-aceticacid

[1042]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperidine-4-aceticacid

[1043]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1044]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-aceticacid

[1045]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1046]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-aceticacid

[1047]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-aceticacid

[1048]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1049]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-aceticacid

[1050]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-aceticacid

[1051]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1052]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1053]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1054]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1055]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1056]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1057]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1058]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1059]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1060]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1061]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1062]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1063]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1064]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1065]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1066]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1067]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-aceticacid

[1068]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1069]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1070]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]-piperidine-4-aceticacid

[1071]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1072]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1073]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1074]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1075]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1076]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1077]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1078]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1079]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1080]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-aceticacid

[1081]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1082]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-aceticacid

[1083]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1084]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1085]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-(2-(cyclopentylthio)-ethyl]piperidine-4-aceticacid

[1086]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thio-ethyl]piperidine-4-aceticacid

[1087]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thio-ethyl]piperidine-4-aceticacid

[1088]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1089]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1090]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1091]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1092]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1093]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1094]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1095]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-aceticacid

[1096]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1097]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1098]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperidine-4-aceticacid

[1099]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperidine-4-aceticacid

[1100]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-aceticacid

[1101]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1102]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1103]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1104]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1105]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1106]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-aceticacid

[1107]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1108]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-aceticacid

[1109]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1110]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1111]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperidine-4-aceticacid

[1112]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1113]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1114]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1115]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1116]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1117]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1118]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1119]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-aceticacid

[1120]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1121]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-aceticacid

[1122]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1123]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1124]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperidine-4-aceticacid

[1125]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1126]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1127]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1128]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1129]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)-ethyl]piperidine-4-aceticacid

[1130]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1131]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1132]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1133]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1134]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-aceticacid

[1135]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1136]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-thio)ethyl]piperidine-4-aceticacid

[1137]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl-thio)ethyl]piperidine-4-aceticacid

[1138]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperidine-4-aceticacid

[1139]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-aceticacid

[1140]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-prop-2-ynyl]piperidine-4-aceticacid

[1141]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1142]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1143]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1144]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1145]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1146]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1147]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]-piperidine-4-aceticacid

[1148]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]-piperidine-4-aceticacid

[1149]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1150]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1151]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]-piperidine-4-aceticacid

[1152]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]-piperidine-4-aceticacid

[1153]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]-piperidine-4-aceticacid

[1154]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]-piperidine-4-aceticacid

[1155]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1156]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1157]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]-piperidine-4-aceticacid

[1158]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]-piperidine-4-aceticacid

[1159]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1160]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1161]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1162]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1163]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1164]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1165]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1166]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1167]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1168]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1169]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1170]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1171]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1172]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1173]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1174]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1175]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1176]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1177]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1178]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1179]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1180]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1181]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1182]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1183]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1184]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1185]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1186]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1187]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]-piperidine-4-aceticacid

[1188]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1189]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1190]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1191]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1192]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1193]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1194]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1195]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperidine-4-aceticacid

[1196]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1197]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-aceticacid

[1198]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1199]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1200]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1201]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-aceticacid

[1202]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1203]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-aceticacid

[1204]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1205]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperidine-4-aceticacid

[1206]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluoro-phenoxy)ethyl]piperidine-4-aceticacid

[1207]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluoro-phenoxy)ethyl]piperidine-4-aceticacid

[1208]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluoro-phenyl)prop-2-ynyl]piperidine-4-aceticacid

[1209]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluoro-phenyl)prop-2-ynyl]piperidine-4-aceticacid

[1210]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-aceticacid

[1211]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]-piperidine-4-aceticacid

[1212]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]-piperidine-4-aceticacid

[1213]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)-propyl]piperidine-4-aceticacid

[1214]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)-propyl]piperidine-4-aceticacid

[1215]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)-propyl]piperidine-4-aceticacid

[1216]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)-butyl]piperidine-4-aceticacid

[1217]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluoro-phenyl)propyl]piperidine-4-aceticacid

[1218]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluoro-phenyl)propyl]piperidine-4-aceticacid

[1219]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluoro-phenyl)propyl]piperidine-4-aceticacid

[1220]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluoro-phenyl)propyl]piperidine-4-aceticacid

[1221]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluoro-phenyl)propyl]piperidine-4-aceticacid

[1222]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1223]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1224]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1225]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthio-propyl]piperidine-4-aceticacid

[1226]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-aceticacid

[1227]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-aceticacid

[1228]314-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-aceticacid

[1229]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-aceticacid

[1230]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperidine-4-aceticacid

[1231]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperidine-4-aceticacid

[1232]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperidine-4-aceticacid

[1233]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1234]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1235]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1236]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1237]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1238]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1239]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1240]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1241]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1242]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1243]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1244]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperidine-4-aceticacid

[1245]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-aceticacid

[1246]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-(2-chlorophenylthio)propyl]piperidine-4-aceticacid

[1247]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-aceticacid

[1248]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-aceticacid

[1249]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-aceticacid

[1250]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-aceticacid

[1251]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-aceticacid

[1252]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperidine-4-aceticacid

[1253]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-aceticacid

[1254]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperidine-4-aceticacid

[1255]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-aceticacid

[1256]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperidine-4-aceticacid

[1257]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]piperidine-4-aceticacid

[1258]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]piperidine-4-aceticacid

[1259]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]piperidine-4-aceticacid

[1260]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]piperidine-4-aceticacid

[1261]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]piperidine-4-aceticacid

[1262]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]piperidine-4-aceticacid

[1263]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperidine-4-aceticacid

[1264]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperidine-4-aceticacid

[1265]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperidine-4-aceticacid

[1266]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperidine-4-aceticacid

[1267]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-aceticacid

[1268]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperidine-4-aceticacid

[1269]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-aceticacid

[1270]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-aceticacid

[1271]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1272]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1273]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-aceticacid

[1274]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-aceticacid

[1275]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1276]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-aceticacid

[1277]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-aceticacid

[1278]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-aceticacid

[1279]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-aceticacid

[1280]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1281]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-aceticacid

[1282]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-aceticacid

[1283]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,³-thiazol-²-yl)propyl]piperidine-4-acetic acid

[1284]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-²-yl)butyl]piperidine-4-aceticacid

[1285]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-acetic acid

[1286]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-aceticacid

[1287]4-[3-(R,S)-Hydroxy-3-(³-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperidine-4-aceticacid

[1288]4-[3-(R,S)-Hydroxy-3-(³-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-aceticacid

[1289]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-aceticacid

[1290]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-aceticacid

[1291]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-aceticacid

[1292]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-aceticacid

[1293]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-aceticacid

[1294]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-aceticacid

[1295]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-aceticacid

[1296]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-aceticacid

[1297]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-aceticacid

[1298]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-aceticacid

[1299]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-acetic acid

[1300]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-aceticacid

[1301]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1302]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1303]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1304]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1305]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1306]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1307]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyll-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1308]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1309]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1310]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1311]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1312]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-aceticacid

[1313]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperidine-4-aceticacid

[1314]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1315]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-aceticacid

[1316]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1317]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-aceticacid

[1318]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-aceticacid

[1319]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1320]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-aceticacid

[1321]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-aceticacid

[1322]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1323]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1324]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1325]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1326]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1327]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1328]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1329]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1330]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1331]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1332]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1333]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1334]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1335]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1336]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1337]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1338]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1339]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1340]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1341]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1342]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1343]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1344]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1345]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1346]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1347]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1348]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1349]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1350]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1351]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1352]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1353]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1354]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1355]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1356]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1357]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1358]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1359]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1360]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1361]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1362]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1363]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1364]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1365]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1366]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1367]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1368]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1369]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1370]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1371]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1372]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1373]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1374]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1375]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1376]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1377]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1378]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1379]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1380]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1381]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1382]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1383]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1384]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1385]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1386]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1387]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1388]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1389]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1390]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1391]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1392]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1393]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1394]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1395]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1396]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1397]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1398]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1399]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1400]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1401]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1402]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1403]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1404]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1405]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1406]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1407]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1408]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1409]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1410]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1411]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1412]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1413]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1414]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1415]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1416]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1417]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1418]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1419]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1420]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1421]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1422]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1423]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1424]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1425]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1426]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1427]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1428]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1429]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1430]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1431]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1432]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1433]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1434]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1435]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1436]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1437]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1438]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1439]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1440]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1441]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1442]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1443]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1444]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1445]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1446]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1447]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1448]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1449]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1450]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1451]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1452]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1453]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1454]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1455]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1456]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1457]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1458]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1459]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1460]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1461]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1462]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1463]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1464]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1465]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1466]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1467]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1468]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1469]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1470]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1471]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1472]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1473]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1474]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1475]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1476]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1477]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1478]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1479]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1480]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1481]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1482]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-aceticacid

[1483]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-aceticacid

[1484]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1485]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-aceticacid

[1486]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-aceticacid

[1487]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperidine-4-aceticacid

[1488]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-aceticacid

[1489]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperidine-4-aceticacid

[1490]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-aceticacid

[1491]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperidine-4-aceticacid

[1492]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-aceticacid

[1493]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-aceticacid

[1494]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1495]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1496]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1497]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthio-propyl]piperidine-4-aceticacid

[1498]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-aceticacid

[1499]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-aceticacid

[1500]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-aceticacid

[1501]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-aceticacid

[1502]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperidine-4-aceticacid

[1503]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperidine-4-aceticacid

[1504]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperidine-4-aceticacid

[1505]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1506]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1507]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1508]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1509]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1510]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1511]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1512]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1513]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1514]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1515]4-(3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1516]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperidine-4-aceticacid

[1517]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-aceticacid

[1518]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-aceticacid

[1519]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-aceticacid

[1520]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-aceticacid

[1521]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-aceticacid

[1522]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-aceticacid

[1523]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-aceticacid

[1524]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperidine-4-aceticacid

[1525]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-aceticacid

[1526]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperidine-4-aceticacid

[1527]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-aceticacid

[1528]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperidine-4-aceticacid

[1529]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]piperidine-4-aceticacid

[1530]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]piperidine-4-aceticacid

[1531]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]piperidine-4-aceticacid

[1532]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]piperidine-4-aceticacid

[1533]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]piperidine-4-aceticacid

[1534]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]piperidine-4-aceticacid

[1535]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperidine-4-aceticacid

[1536]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperidine-4-aceticacid

[1537]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperidine-4-aceticacid

[1538]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperidine-4-aceticacid

[1539]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-aceticacid

[1540]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperidine-4-aceticacid

[1541]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-aceticacid

[1542]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-aceticacid

[1543]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1544]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1545]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-aceticacid

[1546]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-aceticacid

[1547]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1548]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-aceticacid

[1549]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-aceticacid

[1550]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-aceticacid

[1551]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-aceticacid

[1552]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1553]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-aceticacid

[1554]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-aceticacid

[1555]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-aceticacid

[1556]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperidine-4-aceticacid

[1557]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-aceticacid

[1558]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-aceticacid

[1559]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperidine-4-aceticacid

[1560]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-aceticacid

[1561]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-aceticacid

[1562]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-aceticacid

[1563]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-aceticacid

[1564]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-aceticacid

[1565]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-aceticacid

[1566]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-aceticacid

[1567]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-aceticacid

[1568]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-aceticacid

[1569]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-aceticacid

[1570]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-aceticacid

[1571]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-aceticacid

[1572]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-aceticacid

[1573]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1574]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1575]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1576]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1577]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1578]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1579]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1580]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1581]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1582]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1583]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1584]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-aceticacid

[1585]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperidine-4-aceticacid

[1586]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1587]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-aceticacid

[1588]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1589]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-aceticacid

[1590]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-aceticacid

[1591]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1592]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-aceticacid

[1593]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-aceticacid

[1594]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1595]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1596]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1597]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1598]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-acetic acid

[1599]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1600]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1601]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1602]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1603]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1604]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1605]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1606]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1607]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1608]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1609]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1610]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-acetic acid

[1611]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1612]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1613]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1614]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1615]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1616]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1617]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1618]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1619]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1620]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1621]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1622]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1623]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1624]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1625]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-acetic acid

[1626]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1627]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1628]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1629]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1630]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1631]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1632]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1633]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1634]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1635]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1636]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1637]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1638]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1639]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-ethoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1640]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1641]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1642]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1643]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1644]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1645]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1646]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1647]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1648]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1649]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1650]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1651]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1652]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1653]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1654]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1655]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1656]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1657]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1658]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1659]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1660]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1661]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1662]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1663]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1664]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1665]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1666]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1667]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1668]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1669]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-aceticacid

[1670]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-aceticacid

[1671]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1672]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-aceticacid

[1673]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1674]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[1675]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1676]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1677]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-aceticacid

[1678]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-aceticacid

[1679]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-(2-(thien-2-yl)thioethyl]piperidine-4-aceticacid

[1680]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1681]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-aceticacid

[1682]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1683]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1684]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1685]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1686]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1687]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1688]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1689]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1690]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1691]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1692]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1693]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1694]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1695]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1696]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1697]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1698]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1699]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1700]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1701]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1702]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1703]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1704]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1705]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1706]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1707]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1708]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1709]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1710]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl)-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1711]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1712]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1713]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1714]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1715]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1716]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1717]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1718]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1719]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1720]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1721]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1722]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1723]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1724]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1725]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1726]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1727]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1728]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-(2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1729]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1730]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1731]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1732]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1733]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1734]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1735]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1736]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl3-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1737]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1738]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1739]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1740]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1741]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-aceticacid

[1742]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-aceticacid

[1743]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1744]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-aceticacid

[1745]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1746]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-aceticacid

[1747]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1748]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-aceticacid

[1749]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1750]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-aceticacid

[1751]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperid-4-ylmethanol

[1752]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperid-4-ylmethanol

[1753]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperid-4-ylmethanol

[1754]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperid-4-ylmethanol

[1755]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperid-4-ylmethanol

[1756]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperid-4-ylmethanol

[1757]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperid-4-ylmethanol

[1758]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperid-4-ylmethanol

[1759]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperid-4-ylmethanol

[1760]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperid-4-ylmethanol

[1761]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperid-4-ylmethanol

[1762]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1763]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1764]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1765]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthiopropyl]piperid-4-ylmethanol

[1766]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperid-4-ylmethanol

[1767]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperid-4-ylmethanol

[1768]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperid-4-ylmethanol

[1769]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperid-4-ylmethanol

[1770]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1771]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl-thio)propyl]piperid-4-ylmethanol

[1772]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1773]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1774]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1775]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1776]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1777]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1778]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1779]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperid-4-ylmethanol

[1780]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[1781]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[1782]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[1783]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)-propyl]piperid-4-ylmethanol

[1784]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperid-4-ylmethanol

[1785]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperid-4-ylmethanol

[1786]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperid-4-ylmethanol

[1787]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperid-4-ylmethanol

[1788]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperid-4-ylmethanol

[1789]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperid-4-ylmethanol

[1790]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperid-4-ylmethanol

[1791]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperid-4-ylmethanol

[1792]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperid-4-ylmethanol

[1793]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperid-4-ylmethanol

[1794]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperid-4-ylmethanol

[1795]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperid-4-ylmethanol

[1796]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)-ethyl]piperid-4-ylmethanol

[1797]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)-propyl]piperid-4-ylmethanol

[1798]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)-ethyl]piperid-4-ylmethanol

[1799]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)-propyl]piperid-4-ylmethanol

[1800]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)-ethyl]piperid-4-ylmethanol

[1801]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)-propyl]piperid-4-ylmethanol

[1802]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperid-4-ylmethanol

[1803]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)-propyl]piperid-4-ylmethanol

[1804]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperid-4-ylmethanol

[1805]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)-propyl]piperid-4-ylmethanol

[1806]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperid-4-ylmethanol

[1807]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)-propyl]piperid-4-ylmethanol

[1808]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperid-4-ylmethanol

[1809]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperid-4-ylmethanol

[1810]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[1811]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperid-4-ylmethanol

[1812]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperid-4-ylmethanol

[1813]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperid-4-ylmethanol

[1814]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperid-4-ylmethanol

[1815]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperid-4-ylmethanol

[1816]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperid-4-ylmethanol

[1817]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperid-4-ylmethanol

[1818]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperid-4-ylmethanol

[1819]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperid-4-ylmethanol

[1820]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperid-4-ylmethanol

[1821]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperid-4-ylmethanol

[1822]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperid-4-ylmethanol

[1823]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperid-4-ylmethanol

[1824]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperid-4-ylmethanol

[1825]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperid-4-ylmethanol

[1826]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperid-4-ylmethanol

[1827]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperid-4-ylmethanol

[1828]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperid-4-ylmethanol

[1829]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperid-4-ylmethanol

[1830]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperid-4-ylmethanol

[1831]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperid-4-ylmethanol

[1832]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperid-4-ylmethanol

[1833]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperid-4-ylmethanol

[1834]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperid-4-ylmethanol

[1835]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperid-4-ylmethanol

[1836]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperid-4-ylmethanol

[1837]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1838]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1839]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1840]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1841]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1842]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1843]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1844]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1845]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1846]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1847]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1848]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperid-4-ylmethanol

[1849]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperid-4-ylmethanol

[1850]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1851]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperid-4-ylmethanol

[1852]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1853]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperid-4-ylmethanol

[1854]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperid-4-ylmethanol

[1855]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1856]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperid-4-ylmethanol

[1857]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperid-4-ylmethanol

[1858]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[1859]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[1860]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[1861]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[1862]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[1863]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[1864]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1865]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[1866]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[1867]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[1868]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1869]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1870]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[1871]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[1872]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1873]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1874]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1875]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[1876]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1877]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1878]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[1879]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[1880]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[1881]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1882]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1883]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[1884]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[1885]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[1886]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-phenylamino)ethyl]piperid-4-ylmethanol

[1887]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-phenylamino)ethyl]piperid-4-ylmethanol

[1888]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperid-4-ylmethanol

[1889]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1890]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1891]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperid-4-ylmethanol

[1892]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperid-4-ylmethanol

[1893]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperid-4-ylmethanol

[1894]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1895]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1896]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[1897]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[1898]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1899]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperid-4-ylmethanol

[1900]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[1901]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperid-4-ylmethanol

[1902]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1903]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1904]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperid-4-ylmethanol

[1905]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thio-ethyl]piperid-4-ylmethanol

[1906]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thio-ethyl]piperid-4-ylmethanol

[1907]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1908]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]-piperid-4-ylmethanol

[1909]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[1910]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[1911]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[1912]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1913]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1914]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperid-4-ylmethanol

[1915]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1916]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1917]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperid-4-ylmethanol

[1918]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[1919]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[1920]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1921]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1922]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[1923]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[1924]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1925]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperid-4-ylmethanol

[1926]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[1927]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperid-4-ylmethanol

[1928]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1929]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1930]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperid-4-ylmethanol

[1931]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[1932]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[1933]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1934]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1935]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)-ethyl]piperid-4-ylmethanol

[1936]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[1937]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1938]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[1939]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1940]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperid-4-ylmethanol

[1941]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1942]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1943]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperid-4-ylmethanol

[1944]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperid-4-ylmethanol

[1945]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperid-4-ylmethanol

[1946]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluoro-phenyl)prop-2-ynyl]piperid-4-ylmethanol

[1947]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[1948]4-[3-(-3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluoro-phenyl)propyl]piperid-4-ylmethanol

[1949]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluoro-phenyl)propyl]piperid-4-ylmethanol

[1950]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1951]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1952]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[1953]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[1954]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1955]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1956]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1957]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1958]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1959]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1960]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1961]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[1962]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1963]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1964]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1965]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1966]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1967]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1968]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1969]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1970]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1971]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1972]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1973]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1974]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1975]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluoro-phenoxy)ethyl]piperid-4-ylmethanol

[1976]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1977]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1978]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluoro-phenyl)propyl]piperid-4-ylmethanol

[1979]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1980]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1981]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1982]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1983]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1984]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1985]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1986]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1987]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[1988]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[1989]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1990]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-thio)ethyl]piperid-4-ylmethanol

[1991]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1992]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[1993]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1994]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[1995]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1996]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[1997]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1998]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[1999]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[2000]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[2001]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[2002]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)-ethyl]piperid-4-ylmethanol

[2003]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[2004]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[2005]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2006]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2007]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperid-4-ylmethanol

[2008]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperid-4-ylmethanol

[2009]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[2010]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperid-4-ylmethanol

[2011]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[2012]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperid-4-ylmethanol

[2013]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[2014]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperid-4-ylmethanol

[2015]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-prop-2-ynyl]piperid-4-ylmethanol

[2016]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-prop-2-ynyl]piperid-4-ylmethanol

[2017]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperid-4-ylmethanol4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperid-4-ylmethanol

[2018]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]-piperid-4-ylmethanol

[2019]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperid-4-ylmethanol

[2020]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperid-4-ylmethanol

[2021]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)-propyl]piperid-4-ylmethanol

[2022]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)-butyl]piperid-4-ylmethanol

[2023]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)-propyl]piperid-4-ylmethanol

[2024]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)-propyl]piperid-4-ylmethanol

[2025]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)-propyl]piperid-4-ylmethanol

[2026]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)-propyl]piperid-4-ylmethanol

[2027]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)-propyl]piperid-4-ylmethanol

[2028]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2029]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthio-propyl]piperid-4-ylmethanol

[2030]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenyl-thio)propyl]piperid-4-ylmethanol

[2031]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenyl-thio)propyl]piperid-4-ylmethanol

[2032]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenyl-thio)ethyl]piperid-4-ylmethanol

[2033]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl-thio)propyl]piperid-4-ylmethanol

[2034]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenyl-thio)ethyl]piperid-4-ylmethanol

[2035]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl-thio)propyl]piperid-4-ylmethanol

[2036]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenyl-thio)ethyl]piperid-4-ylmethanol

[2037]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2038]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2039]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2040]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-phenoxy)ethyl]piperid-4-ylmethanol

[2041]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-phenoxy)ethyl]piperid-4-ylmethanol

[2042]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluoro-phenoxy)ethyl]piperid-4-ylmethanol

[2043]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluoro-phenoxy)ethyl]piperid-4-ylmethanol

[2044]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-phenylamino)ethyl]piperid-4-ylmethanol

[2045]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-phenylamino)ethyl]piperid-4-ylmethanol

[2046]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluoro-phenylamino)ethyl]piperid-4-ylmethanol

[2047]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluoro-phenylamino)ethyl]piperid-4-ylmethanol

[2048]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluoro-phenylthio)propyl]piperid-4-ylmethanol

[2049]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chloro-phenylthio)ethyl]piperid-4-ylmethanol

[2050]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-phenylthio)propyl]piperid-4-ylmethanol

[2051]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chloro-phenylthio)ethyl]piperid-4-ylmethanol

[2052]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-phenylthio)propyl]piperid-4-ylmethanol

[2053]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chloro-phenylthio)ethyl]piperid-4-ylmethanol

[2054]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-phenylthio)propyl]piperid-4-ylmethanol

[2055]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenyl-thio)ethyl]piperid-4-ylmethanol

[2056]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenyl-thio)propyl]piperid-4-ylmethanol

[2057]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenyl-thio)ethyl]piperid-4-ylmethanol

[2058]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenyl-thio)propyl]piperid-4-ylmethanol

[2059]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenyl-thio)ethyl]piperid-4-ylmethanol

[2060]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenyl-thio)propyl]piperid-4-ylmethanol

[2061]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethyl-phenylthio)ethyl]piperid-4-ylmethanol

[2062]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethyl-phenylthio)propyl]piperid-4-ylmethanol

[2063]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethyl-phenylthio)ethyl]piperid-4-ylmethanol

[2064]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethyl-phenylthio)propyl]piperid-4-ylmethanol

[2065]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethyl-phenylthio)ethyl]piperid-4-ylmethanol

[2066]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethyl-phenylthio)propyl]piperid-4-ylmethanol

[2067]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenyl-thio)ethyl]piperid-4-ylmethanol

[2068]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenyl-thio)propyl]piperid-4-ylmethanol

[2069]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenyl-thio)ethyl]piperid-4-ylmethanol

[2070]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenyl-thio)propyl]piperid-4-ylmethanol

[2071]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenyl-thio)ethyl]piperid-4-ylmethanol

[2072]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenyl-thio)propyl]piperid-4-ylmethanol

[2073]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]-piperid-4-ylmethanol

[2074]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]-piperid-4-ylmethanol

[2075]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]-piperid-4-ylmethanol

[2076]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2077]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)-propyl]piperid-4-ylmethanol

[2078]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperid-4-ylmethanol

[2079]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2080]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperid-4-ylmethanol

[2081]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperid-4-ylmethanol

[2082]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperid-4-ylmethanol

[2083]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperid-4-ylmethanol

[2084]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2085]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperid-4-ylmethanol

[2086]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperid-4-ylmethanol

[2087]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperid-4-ylmethanol

[2088]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperid-4-ylmethanol

[2089]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperid-4-ylmethanol

[2090]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperid-4-ylmethanol

[2091]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperid-4-ylmethanol

[2092]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperid-4-ylmethanol

[2093]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperid-4-ylmethanol

[2094]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperid-4-ylmethanol

[2095]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperid-4-ylmethanol

[2096]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperid-4-ylmethanol

[2097]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperid-4-ylmethanol

[2098]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperid-4-ylmethanol

[2099]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperid-4-ylmethanol

[2100]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperid-4-ylmethanol

[2101]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperid-4-ylmethanol

[2102]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperid-4-ylmethanol

[2103]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperid-4-ylmethanol

[2104]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2105]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2106]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2107]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2108]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2109]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2110]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2111]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2112]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2113]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2114]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2115]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperid-4-ylmethanol

[2116]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperid-4-ylmethanol

[2117]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2118]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperid-4-ylmethanol

[2119]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2120]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperid-4-ylmethanol

[2121]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperid-4-ylmethanol

[2122]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2123]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperid-4-ylmethanol

[2124]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperid-4-ylmethanol

[2125]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2126]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2127]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2128]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2129]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2130]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2131]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2132]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2133]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2134]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2135]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2136]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2137]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2138]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2139]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2140]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2141]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2142]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2143]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2144]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2145]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2146]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2147]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2148]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2149]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2150]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2151]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2152]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2153]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-(3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2154]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2155]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2156]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2157]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2158]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2159]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2160]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2161]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2162]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2163]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2164]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2165]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2166]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2167]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2168]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2169]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2170]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2171]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2172]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2173]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2174]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2175]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2176]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2177]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2178]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2179]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2180]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2181]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2182]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2183]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2184]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2185]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2186]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2187]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2188]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2189]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2190]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2191]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2192]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2193]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2194]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2195]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2196]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2197]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2198]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2199]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2200]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2201]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2202]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2203]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2204]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2205]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2206]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2207]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2208]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2209]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2210]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2211]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2212]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2213]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2214]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2215]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2216]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2217]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2218]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2219]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2220]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2221]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2222]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2223]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2224]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2225]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2226]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl)piperid-4-ylmethanol

[2227]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2228]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2229]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2230]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2231]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2232]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2233]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2234]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2235]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2236]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2237]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2238]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2239]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2240]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2241]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2242]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2243]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2244]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2245]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2246]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2247]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2248]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2249]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2250]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2251]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2252]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2253]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2254]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2255]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2256]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2257]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2258]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2259]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2260]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2261]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2262]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2263]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2264]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2265]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2266]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2267]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2268]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2269]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2270]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2271]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2272]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2273]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2274]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2275]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2276]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2277]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2278]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2279]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2280]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2281]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2282]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2283]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2284]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2285]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperid-4-ylmethanol

[2286]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperid-4-ylmethanol

[2287]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2288]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperid-4-ylmethanol

[2289]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperid-4-ylmethanol

[2290]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperid-4-ylmethanol

[2291]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperid-4-ylmethanol

[2292]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperid-4-ylmethanol

[2293]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperid-4-ylmethanol

[2294]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperid-4-ylmethanol

[2295]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperid-4-ylmethanol

[2296]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperid-4-ylmethanol

[2297]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2298]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2299]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2300]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthio-propyl]piperid-4-ylmethanol

[2301]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperid-4-ylmethanol

[2302]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperid-4-ylmethanol

[2303]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperid-4-ylmethanol

[2304]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperid-4-ylmethanol

[2305]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperid-4-ylmethanol

[2306]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperid-4-ylmethanol

[2307]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperid-4-ylmethanol

[2308]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2309]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2310]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2311]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2312]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2313]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2314]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2315]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2316]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2317]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2318]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2319]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperid-4-ylmethanol

[2320]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperid-4-ylmethanol

[2321]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperid-4-ylmethanol

[2322]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperid-4-ylmethanol

[2323]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperid-4-ylmethanol

[2324]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperid-4-ylmethanol

[2325]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperid-4-ylmethanol

[2326]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperid-4-ylmethanol

[2327]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperid-4-ylmethanol

[2328]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperid-4-ylmethanol

[2329]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperid-4-ylmethanol

[2330]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperid-4-ylmethanol

[2331]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperid-4-ylmethanol

[2332]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]piperid-4-ylmethanol

[2333]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]piperid-4-ylmethanol

[2334]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]piperid-4-ylmethanol

[2335]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]piperid-4-ylmethanol

[2336]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]piperid-4-ylmethanol

[2337]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]piperid-4-ylmethanol

[2338]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperid-4-ylmethanol

[2339]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperid-4-ylmethanol

[2340]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperid-4-ylmethanol

[2341]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperid-4-ylmethanol

[2342]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperid-4-ylmethanol

[2343]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperid-4-ylmethanol

[2344]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperid-4-ylmethanol

[2345]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperid-4-ylmethanol

[2346]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)-ethyl]piperid-4-ylmethanol

[2347]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperid-4-ylmethanol

[2348]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)-propyl]piperid-4-ylmethanol

[2349]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)-propyl]piperid-4-ylmethanol

[2350]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperid-4-ylmethanol

[2351]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]-piperid-4-ylmethanol

[2352]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]-piperid-4-ylmethanol

[2353]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]-piperid-4-ylmethanol

[2354]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]-piperid-4-ylmethanol

[2355]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperid-4-ylmethanol

[2356]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]-piperid-4-ylmethanol

[2357]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]-piperid-4-ylmethanol

[2358]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperid-4-ylmethanol

[2359]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperid-4-ylmethanol

[2360]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperid-4-ylmethanol

[2361]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperid-4-ylmethanol

[2362]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperid-4-ylmethanol

[2363]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperid-4-ylmethanol

[2364]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperid-4-ylmethanol

[2365]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperid-4-ylmethanol

[2366]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperid-4-ylmethanol

[2367]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperid-4-ylmethanol

[2368]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperid-4-ylmethanol

[2369]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperid-4-ylmethanol

[2370]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperid-4-ylmethanol

[2371]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperid-4-ylmethanol

[2372]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperid-4-ylmethanol

[2373]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperid-4-ylmethanol

[2374]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperid-4-ylmethanol

[2375]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperid-4-ylmethanol

[2376]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2377]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2378]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2379]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2380]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2381]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2382]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2383]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2384]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2385]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2386]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2387]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperid-4-ylmethanol

[2388]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bis(trifluoromethyl)phenyl)prop-2-ynyl]piperid-4-ylmethanol

[2389]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2390]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperid-4-ylmethanol

[2391]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2392]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperid-4-ylmethanol

[2393]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperid-4-ylmethanol

[2394]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2395]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperid-4-ylmethanol

[2396]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperid-4-ylmethanol

[2397]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2398]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2399]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2400]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2401]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2402]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2403]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2404]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2405]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2406]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2407]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2408]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2409]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2410]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2411]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2412]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2413]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2414]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2415]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2416]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2417]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2418]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2419]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2420]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2421]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2422]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2423]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2424]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2425]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2426]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2427]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2428]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2429]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2430]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2431]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2432]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2433]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2434]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2435]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2436]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2437]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2438]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2439]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2440]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2441]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2442]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2443]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2444]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2445]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2446]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2447]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2448] 4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2449]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2450]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2451]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2452]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2453]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2454]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2455]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2456]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2457]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2458]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2459]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2460]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2461]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2462]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2463] 4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2464]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2465]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2466]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2467]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2468]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2469]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2470]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2471]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2472]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2473]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2474]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2475]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperid-4-ylmethanol

[2476]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperid-4-ylmethanol

[2477]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2478]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperid-4-ylmethanol

[2479]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2480]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperid-4-ylmethanol

[2481]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2482]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2483]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperid-4-ylmethanol

[2484]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperid-4-ylmethanol

[2485]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperid-4-ylmethanol

[2486]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2487]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperid-4-ylmethanol

[2488]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2489]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2490]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2491]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2492]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2493]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2494]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2495]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2496]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2497]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2498]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2499]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2500]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2501]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2502]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2503]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2504]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2505]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2506]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2507]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2508]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2509]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2510]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2511]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-(2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2512]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2513]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2514]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2515]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2516]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl)piperid-4-ylmethanol

[2517]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2518]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2519]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2520]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2521]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2522]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2523]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2524]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2525]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2526]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2527]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2528]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2529]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2530]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2531]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2532]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2533]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2534]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2535]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2536]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2537]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2538]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2539]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2540]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2541]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2542]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2543]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2544]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2545]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2546]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2547]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2548]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperid-4-ylmethanol

[2549]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperid-4-ylmethanol

[2550]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2551]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperid-4-ylmethanol

[2552]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2553]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperid-4-ylmethanol

[2554]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl)piperid-4-ylmethanol

[2555]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperid-4-ylmethanol

[2556]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2557]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperid-4-ylmethanol

[2558] 4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-hydroxamic acid

[2559]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-hydroxamicacid

[2560]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[2561]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[2562]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[2563]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-hydroxamicacid

[2564]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2565]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2566]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2567]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2568]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2569]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2570]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2571]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2572]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthiopropyl]piperidine-4-hydroxamicacid

[2573]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2574]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2575]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2576]4-(3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2577]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2578]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2579]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2580]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2581]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2582]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2583]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2584]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2585]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2586]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2587]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2588]4-(3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2589]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2590]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2591]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2592]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[2593]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2594]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[2595]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2596]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[2597]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2598]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[2599]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2600]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[2601]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2602]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[2603]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2604]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]piperidine-4-hydroxamicacid

[2605]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2606]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]piperidine-4-hydroxamicacid

[2607]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2608]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]piperidine-4-hydroxamicacid

[2609]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[2610]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[2611]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[2612]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[2613]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[2614]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[2615]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-hydroxamicacid

[2616]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-hydroxamicacid

[2617]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2618]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-hydroxamicacid

[2619]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-hydroxamicacid

[2620]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-hydroxamicacid

[2621]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[2622]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-hydroxamicacid

[2623]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-hydroxamicacid

[2624]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-hydroxamicacid

[2625]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-hydroxamicacid

[2626]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-hydroxamicacid

[2627]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperidine-4-hydroxamicacid

[2628]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2629]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-hydroxamicacid

[2630]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl]piperidine-4-hydroxamicacid

[2631]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[2632]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-hydroxamicacid

[2633]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-hydroxamicacid

[2634]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-hydroxamicacid

[2635]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-hydroxamicacid

[2636]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-hydroxamicacid

[2637]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-hydroxamicacid

[2638]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-hydroxamicacid

[2639]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-hydroxamicacid

[2640]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-hydroxamicacid

[2641]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-hydroxamicacid

[2642]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2643]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[2644]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2645]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2646]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2647]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2648]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2649]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2650]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2651]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2652]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2653]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2654]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2655]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2656]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bistrifluoromethylphenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2657]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2658]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)-2-ynyl]piperidine-4-hydroxamicacid

[2659]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2660]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2661]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2662]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2663]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2664]4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2665]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2666]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2667]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2668]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2669]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2670]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2671]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2672]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2673]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2674]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2675]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2676]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2677]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2678]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2679]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2680]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2681]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2682]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2683]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2684]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2685]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2686]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2687]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2688]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2689]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2690]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2691]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2692]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2693]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2694]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2695]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2696]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2697]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2698]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2699]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2700]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2701]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2702]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2703]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2704]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2705]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2706]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2707]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2708]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2709]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2710]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2711]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2712]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2713]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2714]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2715]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2716]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2717]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2718]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2719]4-(3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2720]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2721]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2722]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2723]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2724]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2725]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2726]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2727]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2728]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2729]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2730]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2731]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2732]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2733]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2734]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2735]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2736]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2737]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2738]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2739]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2740]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2741]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2742]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2743]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2744]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2745]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2746]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2747]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2748]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2749]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2750]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthiol)ethyl]piperidine-4-hydroxamicacid

[2751]4-(3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2752]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2753]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2754]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2755]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2756]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2757]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2758]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2759]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2760]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2761]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2762]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2763]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2764]4-[3-(3-Methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2765]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2766]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2767]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2768]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2769]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2770]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2771]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2772]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2773]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2774]4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2775]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2776]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2777]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2778]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2779]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2780]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2781]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2782]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2783]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2784]4-[3-(3-Dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2785]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2786]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2787]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-(2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2788]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2789]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2790]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2791]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2792]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2793]4-[3-(3-Hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2794]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2795]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2796]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2797]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2798]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2799]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2800]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2801]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2802]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2803]4-[3-(3-Fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2804]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2805]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2806]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2807]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2808]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2809]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2810]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2811]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2812]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2813]4-[3-(3-Aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2814]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2815]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2816]4-(3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2817]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2818]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2819]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2820]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2821]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2822]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2823]4-[3-(3-Morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2824]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-hydroxamic acid

[2825]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-hydroxamicacid

[2826]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2827]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[2828]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[2829]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[2830]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-hydroxamicacid

[2831]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2832]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2833]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-(2,6-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2834]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2835]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[2836]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2837]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthiopropyl]piperidine-4-hydroxamicacid

[2838]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2839]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2840]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2841]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2842]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2843]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2844]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2845]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2846]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2847]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2848]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2849]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2850]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2851]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2852]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2853]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2854]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2855]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2856]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperidine-4-hydroxamicacid

[2857]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2858]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[2859]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2860]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[2861]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2862]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[2863]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2864]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[2865]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2866]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[2867]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2868]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[2869]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2870]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]piperidine-4-hydroxamicacid

[2871]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2872]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]piperidine-4-hydroxamicacid

[2873]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]piperidine-4-hydroxamicacid

[2874]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]piperidine-4-hydroxamicacid

[2875]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[2876]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[2877]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[2878]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[2879]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[2880]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[2881]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-hydroxamicacid

[2882]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-hydroxamicacid

[2883]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2884]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2885]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-hydroxamicacid

[2886]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-hydroxamicacid

[2887]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2888]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-hydroxamicacid

[2889]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[2890]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-hydroxamicacid

[2891]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-hydroxamicacid

[2892]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2893]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-hydroxamicacid

[2894]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-hydroxamicacid

[2895]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-hydroxamicacid

[2896]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(1,3-thiazol-2-yl)butyl]piperidine-4-hydroxamicacid

[2897]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2898]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-hydroxamicacid

[2899]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1[-4-(pyrid-2-yl)butyl]piperidine-4-hydroxamicacid

[2900]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[2901]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-hydroxamicacid

[2902]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-hydroxamicacid

[2903]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-hydroxamicacid

[2904]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-hydroxamicacid

[2905]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-hydroxamicacid

[2906]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-hydroxamicacid

[2907]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-hydroxamicacid

[2908]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-hydroxamicacid

[2909]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-hydroxamicacid

[2910]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-hydroxamicacid

[2911]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2912]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[2913]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2914]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2915]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2916]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2917]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2918]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2919]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2920]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2921]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2922]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2923]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2924]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2925]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bistrifluoromethylphenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2926]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2927]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2928]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2929]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2930]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2931]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2932]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2933]4-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2934]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2935]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2936]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2937]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2938]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2939]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)-propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2940]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2941]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2942]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2943]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2944]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2945]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2946]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2947]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2948]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2949]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2950]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2951]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2952]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2953]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2954]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2955]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2956]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2957]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2958]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2959]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2960]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]-piperidine-4-hydroxamicacid

[2961]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2962]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[2963]4-(3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-hydroxamicacid

[2964]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[2965]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-hydroxamicacid

[2966]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[2967]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[2968]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-hydroxamicacid

[2969]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[2970]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[2971]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2972]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2973]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]-piperidine-4-hydroxamicacid

[2974]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2975]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[2976]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-hydroxamicacid

[2977]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[2978]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-hydroxamicacid

[2979]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[2980]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[2981]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-hydroxamicacid

[2982]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[2983]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[2984]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-prop-2-ynyl]piperidine-4-hydroxamicacid

[2985]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[2986]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[2987]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[2988]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[2989]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2990]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[2991]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-hydroxamicacid

[2992]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[2993]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[2994]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[2995]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2996]4-(3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[2997]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2998]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[2999]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3000]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-(3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3001]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-(3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3002]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3003]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3004]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-hydroxamicacid

[3005]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3006]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3007]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[3008]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3009]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3010]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3011]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3012]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]-piperidine-4-hydroxamicacid

[3013]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3014]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3015]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-hydroxamicacid

[3016]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3017]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3018]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3019]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3020]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-hydroxamicacid

[3021]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[3022]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[3023]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-prop-2-ynyl]piperidine-4-hydroxamicacid

[3024]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3025]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3026]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3027]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3028]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3029]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3030]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3031]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3032]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3033]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3034]4-[3-(R,S)-Hydroxy-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3035]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3036]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3037]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3038]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3039]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3040]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3041]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3042]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3043]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3044]4-[3-(R,S)-Hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3045]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3046]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]-piperidine-4-hydroxamicacid

[3047]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3048]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]-piperidine-4-hydroxamicacid

[3049]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3050]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3051]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3052]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-(2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3053]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3054]4-[3-(R,S)-Hydroxy-3-(3-dimethylamino-6-methoxy-quinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3055]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3056]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3057]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3058]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3059]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3060]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3061]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3062]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3063]4-[3-(R,S)-Hydroxy-3-(3-hydroxymethyl-6-methoxy-quinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3064]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3065]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3066]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3067]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3068]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3069]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3070]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3071]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-(2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3072]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3073]4-[3-(R,S)-Hydroxy-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3074]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3075]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3076]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3077]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3078]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3079]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3080]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3081]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3082]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3083]4-[3-(R,S)-Hydroxy-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3084]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3085]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3086]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3087]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3088]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3089]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3090]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3091]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3092]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-prop-2-ynyl]piperidine-4-hydroxamicacid

[3093]4-[3-(R,S)-Hydroxy-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-prop-2-ynyl]piperidine-4-hydroxamicacid

[3094]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-hydroxamicacid

[3095]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-phenylbutyl]piperidine-4-hydroxamicacid

[3096]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3097]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[3098]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(3-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[3099]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-(4-fluorophenyl)propyl]piperidine-4-hydroxamicacid

[3100]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(4-fluorophenyl)butyl]piperidine-4-hydroxamicacid

[3101]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-(2,3-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[3102]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,3-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[3103]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[3104]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(2,6-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[3105]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-difluorophenyl)propyl]piperidine-4-hydroxamicacid

[3106]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3107]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3108]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3109]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-phenylthiopropyl]piperidine-4-hydroxamicacid

[3110]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[3111]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[3112]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-fluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3113]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenylthio)propyl]piperidine-4-hydroxamicacid

[3114]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3115]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3-difluorophenylthio)propyl]piperidine-4-hydroxamicacid

[3116]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3117]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3118]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3119]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3120]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3121]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3122]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3123]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3124]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3125]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3126]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3127]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3128]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,6-difluorophenylthio)propyl]piperidine-4-hydroxamicacid

[3129]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3130]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[3131]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3132]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[3133]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-chlorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3134]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chlorophenylthio)propyl]piperidine-4-hydroxamicacid

[3135]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[3136]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[3137]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[3138]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[3139]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenylthio)ethyl]piperidine-4-hydroxamicacid

[3140]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methylphenylthio)propyl]piperidine-4-hydroxamicacid

[3141]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-trifluoromethylphenylthio)ethyl]-piperidine-4-hydroxamicacid

[3142]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-trifluoromethylphenylthio)propyl]-piperidine-4-hydroxamicacid

[3143]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-trifluoromethylphenylthio)ethyl]-piperidine-4-hydroxamicacid

[3144]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-trifluoromethylphenylthio)propyl]-piperidine-4-hydroxamicacid

[3145]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-trifluoromethylphenylthio)ethyl]-piperidine-4-hydroxamicacid

[3146]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-trifluoromethylphenylthio)propyl]-piperidine-4-hydroxamicacid

[3147]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[3148]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[3149]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[3150]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[3151]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methoxyphenylthio)ethyl]piperidine-4-hydroxamicacid

[3152]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-methoxyphenylthio)propyl]piperidine-4-hydroxamicacid

[3153]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[cyclopentylmethyl]piperidine-4-hydroxamicacid

[3154]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentyl)ethyl]piperidine-4-hydroxamicacid

[3155]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3156]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[3157]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclopentylthio)propyl]piperidine-4-hydroxamicacid

[3158]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(cyclohexylthio)propyl]piperidine-4-hydroxamicacid

[3159]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3160]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-2-yl)butyl]piperidine-4-hydroxamicacid

[3161]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[3162]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)propyl]piperidine-4-hydroxamicacid

[3163]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(thien-3-yl)butyl]piperidine-4-hydroxamicacid

[3164]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3165]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidine-4-hydroxamicacid

[3166]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)thiopropyl]piperidine-4-hydroxamicacid

[3167]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)propyl]piperidine-4-hydroxamicacid

[3168]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(4-(1,3-thiazol-2-yl)butyl]piperidine-4-hydroxamicacid

[3169]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3170]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)propyl]piperidine-4-hydroxamicacid

[3171]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-2-yl)butyl)piperidine-4-hydroxamicacid

[3172]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[3173]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)propyl]piperidine-4-hydroxamicacid

[3174]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-3-yl)butyl]piperidine-4-hydroxamicacid

[3175]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-3-yl)thioethyl]piperidine-4-hydroxamicacid

[3176]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)thiopropyl]piperidine-4-hydroxamicacid

[3177]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)propyl]piperidine-4-hydroxamicacid

[3178]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrid-4-yl)butyl]piperidine-4-hydroxamicacid

[3179]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-4-yl)thioethyl]piperidine-4-hydroxamicacid

[3180]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)thiopropyl]piperidine-4-hydroxamicacid

[3181]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)propyl]piperidine-4-hydroxamicacid

[3182]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[4-(pyrazin-2-yl)butyl]piperidine-4-hydroxamicacid

[3183]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrazin-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3184]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrazin-2-yl)thiopropyl]piperidine-4-hydroxamicacid

[3185]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3186]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4-difluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3187]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4-difluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3188]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3189]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3190]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3191]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-3-fluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3192]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-4-fluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3193]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2-chloro-4-fluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3194]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-chloro-5-fluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3195]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(4-chloro-2-fluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3196]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluoro-4-methylphenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3197]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,5-bistrifluoromethylphenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3198]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3199]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3200]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3201]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-4-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3202]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(1,3-thiazol-5-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3203]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3204]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-3-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3205]4-[3-(R,S)-Fluoro-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[3-(pyrid-4-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3206]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3207]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3208]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3209]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3210]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3211]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3212]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3213]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3214]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[3215]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3216]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3217]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3218]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3219]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3220]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3221]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3222]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3223]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3224]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3225]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3226]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3227]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[3228]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3229]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3230]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3231]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3232]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3233]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3234]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3235]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3236]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3237]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-hydroxamicacid

[3238]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3239]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3240]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-hydroxamicacid

[3241]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3242]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3243]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3244]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3245]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3246]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3247]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3248]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3249]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3250]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-hydroxamicacid

[3251]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3252]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3253]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[3254]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3255]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3256]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3257]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3258]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3259]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3260]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3261]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3262]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3263]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxyl)ethyl]-piperidine-4-hydroxamicacid

[3264]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-(2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3265]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3266]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-hydroxamicacid

[3267]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3268]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3269]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3270]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3271]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3272]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3273]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3274]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3275]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3276]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3277]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3278]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3279]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-hydroxamicacid

[3280]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3281]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-hydroxamicacid

[3282]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3283]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3284]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-(2-(cyclohexyl)ethyl]piperidine-4-hydroxamicacid

[3285]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(phenyl)propyl]piperidine-4-hydroxamicacid

[3286]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3287]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)-ethyl]piperidine-4-hydroxamicacid

[3288]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3289]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3290]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3291]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenyl-thio)ethyl]piperidine-4-hydroxamicacid

[3292]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-hydroxamicacid

[3293]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[3294]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-hydroxamicacid

[3295]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3296]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-2-yl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3297]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3298]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3299]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3300]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3301]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3302]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3303]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3304]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3305]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3306]4-[3-(R,S)-Fluoro-3-(3-methyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3307]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3308]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3309]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3310]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3311]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3312]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]-piperidine-4-hydroxamicacid

[3313]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3314]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3315]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3316]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]-piperidine-4-hydroxamicacid

[3317]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3318]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3319]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3320]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3321]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3322]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3323]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3324]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3325]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3326]4-[3-(R,S)-Fluoro-3-(3-dimethylamino-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3327]4-[3-(R,S)-Fluoro-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3328]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3329]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3330]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3331]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3332]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3333]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3334]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3335]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3336]4-[3-(R,S)-Fluoro-3-(3-hydroxymethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3337]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3338]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3339]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3340]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3341]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3342]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3343]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3344]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3345]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3346]4-[3-(R,S)-Fluoro-3-(3-fluoromethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3347]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3348]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-hydroxamicacid

[3349]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3350]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)ethyl]piperidine-4-hydroxamicacid

[3351]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3352]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylamino)ethyl]piperidine-4-hydroxamicacid

[3353]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3354]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3355]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3356]4-[3-(R,S)-Fluoro-3-(3-aminomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-hydroxamicacid

[3357]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3358]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-propyl]piperidine-4-hydroxamicacid

[3359]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3360]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenylthio)-ethyl]piperidine-4-hydroxamicacid

[3361]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3362]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenyl-amino)ethyl]piperidine-4-hydroxamicacid

[3363]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,4,6-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3364]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)-ethyl]piperidine-4-hydroxamicacid

[3365]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,4,6-trifluorophenyl)-prop-2-ynyl]piperidine-4-hydroxamicacid

[3366]4-[3-(R,S)-Fluoro-3-(3-morpholinomethyl-6-methoxyquinolin-4-yl)propyl]-1-[3-(3,4,5-trifluorophenyl)-prop-2-ynyl]piperidine-4-hydroxamic acid

[3367]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2-fluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3368]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(3-fluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3369]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(4-fluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3370]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,3-difluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3371]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,4-difluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3372]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,6-difluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3373] 4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(3,5-difluorophenyl)-allyl]-piperidin-4-carboxylic acid

[3374]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(3,4-difluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3375]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,3,5-trifluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3376]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,3,4-trifluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3377]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,3,6-trifluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3378]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,4,5-trifluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3379]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(2,4,6-trifluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3380]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(3,4,5-trifluorophenyl)-allyl]-piperidin-4-carboxylicacid

[3381]4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)-propyl]-1-[3-(3,5,6-trifluorophenyl)-allyl]-piperidin-4-carboxylicacid.

[3382] The examples which follow, given in a non-limiting manner,illustrate the present invention.

EXAMPLE 14-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-carboxylicacid dihydrochloride

[3383] A mixture of 0.6 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-carboxylatein 7.72 cm³ of aqueous 6N hydrochloric acid was maintained at atemperature in the region of 100° C. with stirring and under an inertatmosphere for 2 hours. After cooling to about 20° C., the reactionmixture was concentrated to dryness under reduced pressure (5 kPa) at atemperature in the region of 40° C.

[3384] The residue obtained was taken up in 10 cm³ of adichloromethane/methanol mixture (90/10 by volume). The mixture wasconcentrated to dryness under the above conditions. 0.58 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid dihydrochloride, was obtained in the form of a beige-colored foammelting at 130° C. with decomposition.

[3385]¹H NMR spectrum (250 MHz, (CD₃)₂SO-d₆ at a temperature of 373 K, δin ppm): from 1.50 to 2.30 (mts: 8H in total); from 2.70 to 3.80 (mts:10H in total); 3.99 (s: 3H); 7.09 (dd, J=5 and 3.5 Hz: 1H); 7.29 (broadd, J=3.5 Hz: 1H); 7.40 (d, J=2.5 Hz: 1H); 7.46 (dd, J=9 and 2.5 Hz: 1H);7.64 (broad d, J=5 Hz: 1H); 7.99 (d, J=9 Hz: 1H); 8.67 (s: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-carboxylate

[3386] A mixture of 0.6 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.36 g of 2-(2-bromoethylthio)thiophene and 0.22 g of potassiumcarbonate in 20 cm³ of acetonitrile was heated for 16 hours at atemperature in the region of 80° C., with stirring and under an inertatmosphere. After cooling to a temperature in the region of 20° C., thereaction mixture was concentrated under reduced pressure (5 kPa) at atemperature in the region of 40° C.

[3387] A residue was obtained, which was purified by chromatography,under a nitrogen pressure of 100 kPa, on a column of silica gel(particle size 40-63μ; diameter 3.5 cm; height 28 cm), eluting with amixture of dichloromethane/methanol (97.5/2.5 by volume) and collecting35-cm³ fractions. Fractions 15 to 20 were combined and then concentratedto dryness under the above conditions. 0.67 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylatewas obtained in the form of an orange-colored viscous oil.

[3388] Infra-red spectrum (CCl₄) 2955; 1727; 1622; 1503; 1229; 1117; 833and 698 cm⁻¹.

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3389] 1.27 cm³ of trifluoroacetic acid were added, with stirring andunder an inert atmosphere, at a temperature in the region of 20° C., toa solution of 2.05 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatein 50 cm³ of dichloromethane. After 30 minutes, a further 1.27 cm³ oftrifluoroacetic acid were added and, after a further 30 minutes, afurther 1.27 cm³ were added. The reaction was completed by a finaladdition of 1.27 cm³ of trifluoroacetic acid. After one hour, thereaction mixture was concentrated under reduced pressure (5 kPa) at atemperature in the region of 40° C.

[3390] The evaporation residue was taken up in 50 cm³ of ethyl acetateand 20 cm³ of water. After addition of 5 g of potassium carbonate andstirring for 5 minutes, phases were allowed to separate by settling andthe organic phase separated out was washed with twice 10 cm³ ofdistilled water and then with 20 cm³ of aqueous 10% (by weight) sodiumchloride solution. After drying over magnesium sulfate and thenfiltration, the organic solution was concentrated under reduced pressure(5 kPa) at a temperature in the region of 40° C.

[3391] The residue obtained was purified by chromatography, under anitrogen pressure of 100 kPa, on a column of silica gel (particle size40-63μ; diameter 3.5 cm; height 30 cm), eluting with a mixture ofdichloromethane/methanol/32% aqueous ammonia (89/10/1 by volume), andcollecting 40-cm³ fractions. Fractions 14 to 23 were combined and thenconcentrated to dryness under the above conditions. 1.36 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewere obtained in the form of a beige-colored solid melting at 95° C.

[3392] Infra-red spectrum (KBr) 2960; 1721; 1621; 1503; 1232; 1115; 829and 744 cm⁻¹.

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate

[3393] 1.98 g of benzyl4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate were cooledto a temperature in the region of −30° C. and 11.32 cm³ of a 0.5Msolution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran were addedwith stirring and under an inert atmosphere. After the addition, thetemperature of the mixture was brought to about 20° C. The solutionobtained was stirred for a further 4 hours, followed by addition of 40cm³ of dioxane, 0.183 g of diphenylphosphinoferrocenepalladium chloride,2 g of 4-bromo-3-chloro-6-methoxyquinoline and 3.0 g of tribasicpotassium phosphate. After stirring for 16 hours at a temperature in theregion of 60° C., the reaction mixture was cooled to about 20° C. andthen filtered. The insoluble material was washed with 3 times 20 cm³ ofethyl acetate and the filtrate and washing waters were then combined andstirred with 40 cm³ of water and 100 cm³ of ethyl acetate. The organicphase was separated out by settling, washed with twice 20 cm³ of waterand then with 40 cm³ of aqueous 10% (by weight) sodium chloridesolution, dried over magnesium sulfate, filtered and concentrated underreduced pressure (5 kPa) at a temperature in the region of 40° C.

[3394] The residue obtained was purified by chromatography, under anitrogen pressure of 100 kPa, on a column of silica gel (particle size40-63μ; diameter 3.5 cm; height 30 cm), eluting with a mixture ofdichloromethane/methanol (98.5/1.5 by volume) and collecting 35-cm³fractions. Fractions 22 to 29 were combined and then concentrated underthe above conditions. 2.09 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatewere obtained in the form of a thick yellow oil.

[3395] Infra-red spectrum (CCl₄) 2930; 1728; 1695; 1622; 1503; 1230;1172; 833 and 697 cm⁻¹.

Benzyl 4-allyl-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

[3396] 15.4 g of potassium carbonate and then 10.6 cm³ of benzyl bromidewere added, at a temperature in the region of 20° C., with stirring andunder an inert atmosphere, to a solution of 20 g of4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylic acid in 200cm³ of dimethylformamide. The mixture was stirred for 16 hours at about20° C. and then filtered. The insoluble material was washed with twice100 cm³ of ethyl acetate. The filtrate and the washing waters werecombined, 250 cm³ of water were added and the mixture was then extractedonce with 500 cm³ and once with 150 cm³ of ethyl acetate. The organicextracts were combined, washed with twice 125 cm³ of aqueous 10% (byweight) sodium chloride solution, dried over magnesium sulfate, filteredand concentrated under reduced pressure (5 kPa) at a temperature in theregion of 40° C.

[3397] An oil was obtained, which was purified by chromatography, undera pressure of 100 kPa of nitrogen, on a column of silica gel (particlesize 40-63μ; diameter 7 cm; height 30 cm), eluting with a mixture ofdichloromethane/methanol (99/1 by volume) and collecting 200-cm³fractions. Fractions 6 to 16 were combined and concentrated to drynessunder reduced pressure (5 kPa) at a temperature in the region of 40° C.25 g of benzyl 4-allyl-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatewere obtained in the form of a pale yellow liquid.

[3398] Infra-red spectrum (CH₂Cl₂): 2980; 1725; 1683; 1426; 1171; 1142;974 and 924 cm⁻¹.

4-Allyl-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid

[3399] 4.44 cm³ of water and then 30.62 g of ethyl4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate predissolvedin 150 cm³ of tetrahydrofuran were added, with stirring and under aninert atmosphere, to a mixture of 48.52 g of potassium tert-butoxide in350 cm³ of tetrahydrofuran, cooled to a temperature in the region of 0°C. After allowing the temperature to return to the region of 20° C., themixture was stirred for 24 hours at this temperature. 300 cm³ ofice-cold water were added to the reaction mixture and the mixture wasthen concentrated to dryness under reduced pressure (5 kPa) at atemperature in the region of 40° C. The aqueous residue was extractedwith 300 cm³ of diethyl ether. After leaving to stand for 16 hours, theaqueous phase was acidified at a pH in the region of 3-4 by addition ofabout 215 cm³ of aqueous hydrochloric acid, and was then extracted withthree times 300 cm³ of diethyl ether.

[3400] The ether extracts were combined, dried over magnesium sulfate,filtered and concentrated to dryness under reduced pressure (5 kPa) at atemperature in the region of 40° C. 26.1 g of4-allyl-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid wereobtained in the form of an off-white solid.

[3401] Mass spectrum: EI m/z=269 M^(+.) m/z=168 (M-C₅H₉O₂)⁺m/z=124(m/z=168-CO₂)⁺ m/z=57 C₄H₉ ⁺ base peak

Ethyl allyl-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

[3402] 70 cm³ of a solution of butyllithium in hexane (2.5Mconcentration) were added, with stirring and under an inert atmosphere,to 150 cm³ of tetrahydrofuran cooled to a temperature in the region of−70° C., followed by addition of 50 cm³ of tetrahydrofuran and 23 cm³ ofdiisopropylamine predissolved in 300 cm³ of tetrahydrofuran. After afurther addition of 50 cm³ of tetrahydrofuran, the mixture was stirredfor 15 minutes at about −70° C., followed by addition of 45.15 g ofethyl de 1-(tert-butyloxycarbonyl)isonipecotate predissolved in 400 cm³of tetrahydrofuran, and finally 50 cm³ of this same solvent. Afterstirring the mixture for 1 hour at a temperature in the region of −70°C., 16.7 cm³ of allyl bromide predissolved in 150 cm³ of tetrahydrofuranwere added and the mixture was then warmed to about 20° C. and stirredfor 17 hours. The mixture was poured into 200 cm³ of saturated aqueousammonium chloride solution and then extracted with about 2 liters ofethyl acetate.

[3403] The combined extracts were dried over sodium sulfate, filteredand concentrated under reduced pressure (5 kPa) at a temperature in theregion of 40° C. An oil was obtained, which was purified bychromatography, under a nitrogen pressure of 100 kPa, on a column ofsilica gel (diameter 12 cm; height 50 cm), eluting with a mixture ofdichloromethane/methanol (99.5/0.5 by volume) and collecting 200-cm³fractions. Fractions 20 to 84 were combined and concentrated underreduced pressure (5 kPa) at a temperature in the region of 40° C. 27.85g of ethyl 4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylatewere obtained in the form of a yellow oil.

[3404] Mass spectrum: EI m/z=297 M^(+.) m/z=240(M-C₄H₉)⁺m/z=196(m/z=240-CO₂)⁺ m/z=168 (m/z=240-CO₂Et)⁺ m/z=124(m/z=168-CO₂)⁺m/z=57 C₄H₉ ⁺ base peak.

Ethyl 1-(tert-butyloxycarbonyl) isonipecotate

[3405] 88.3 cm³ of triethylamine were added over 1 hour, with stirringand under an inert atmosphere, to a solution of 100 g of ethylisonipecotate in 1500 cm³ of dichloromethane cooled to a temperature inthe region of 5° C., followed, over the same time, by addition of 166.6g of di-tert-butyl dicarbonate predissolved in 300 cm³ ofdichloromethane. The reaction mixture was stirred for 16 hours whileallowing the temperature to return to the region of 20° C. After afurther addition of 41.6 g of di-tert-butyl dicarbonate dissolved in 70cm³ of dichloromethane, the reaction mixture was stirred for 3 hours atabout 20° C. and then washed with twice 600 cm³ of saturated aqueoussodium chloride solution, dried over sodium sulfate, filtered andconcentrated under reduced pressure (5 kPa) at a temperature in theregion of 40° C. 171 g of ethyl 1-(tert-butyloxycarbonyl)isonipecotatewere obtained in the form of a brown oil.

[3406] Mass spectrum: DCI m/z=275 MNH₄ ⁺ base peak m/z=258 MH⁺.

[3407] 2-(2-Bromoethylsulfanyl)thiophene may be prepared according toSadykhov, K. I., Aliev, S. M. and Seidov, M. M. Khim. Geterotsikl.Soedin, 3, 344-5 (1975).

4-Bromo-3-chloro-6-methoxyquinoline

[3408] A mixture of 20 g of 3-chloro-4-hydroxy-6-methoxyquinoline in1000 cm³ of acetonitrile, to which was added 80.8 g oftriphenylphosphine bromide, was stirred for 2 hours 30 minutes at atemperature in the region of 85° C. The solution obtained was cooled tothe region of 20° C and then stirred for 16 hours at this sametemperature. The reaction mixture was concentrated under reducedpressure (5 kPa) at a temperature in the region of 40° C. and theevaporation residue was then taken up in 200 cm³ of saturated aqueoussodium hydrogen carbonate solution and 200 cm³ of ethyl acetate.

[3409] The organic phase was separated out after settling has takenplace and was washed with twice 200 cm³ of distilled water. The aqueousphase was extracted once more with ethyl acetate and the organicextracts were then combined, dried over magnesium sulfate, filtered andconcentrated under reduced pressure (5 kPa) at a temperature in theregion of 40° C. A product was obtained, which was purified bychromatography under a nitrogen pressure of 100 kPa, on a column ofsilica gel (diameter 7.5 cm; mass of silica 700 g), eluting with amixture of cyclohexane/ethyl acetate (70/30 by volume). The fractionscorresponding to the expected product were collected.

[3410] These fractions were combined and then concentrated under thesame conditions as above. 20.7 g of 4-bromo-3-chloro-6-methoxyquinolinewere obtained in the form of a white solid melting at 108° C.

[3411] Mass spectrum: EI m/z=271 M^(+.) base peak m/z=256 (M-CH₃)⁺m/z=228 (m/z=256-CO)⁺ m/z=149 (m/z=228-Br)^(+.) m/z=114(m/z=149-Cl)^(+.)

3-Chloro-4-hydroxy-6-methoxyquinoline

[3412] 14.26 g of N-chlorosuccinimide were added, at a temperature inthe region of 20° C. and with stirring, to a mixture of 17 g of4-hydroxy-6-methoxyquinoline in 700 cm³ of acetic acid and the mixturewas then heated at a temperature of between 50 and 70° C. for 4 hours.The solution obtained was subsequently cooled to about 20° C. and thenconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 40° C.

[3413] The solid residue was taken up in 250 cm³ of saturated aqueoussodium hydrogen carbonate solution. The mixture was stirred for 1 hour.The insoluble material was filtered off and washed with 3 times 250 cm³of water. The crystals obtained were dried under reduced pressure (10Pa) for 3 hours at a temperature in the region of 20° C. 20 g of3-chloro-4-hydroxy-6-methoxyquinoline were obtained in the form of ayellow solid.

[3414] Mass spectrum: EI m/z=209 M^(+.) base peak m/z=194 (M-CH₃)⁺m/z=166 (m/z=194-CO)⁺.

4-Hydroxy-6-methoxyquinoline

[3415] A suspension of 53.5 g of4-hydroxy-6-methoxy-quinoline-3-carboxylic acid in 1000 cm³ of diphenylether was heated with stirring, at a temperature of between 250° C. and260° C., for 2 hours 45 minutes. The reaction mixture was cooled toabout 20° C. After stirring for 16 hours at this temperature, themixture was poured with stirring into 1 liter of pentane and thenfiltered. The cake obtained was washed with 3 times 100 cm³ of pentaneand then with 3 times 100 cm³ of diisopropyl ether. After drying in air,37 g of 4-hydroxy-6-methoxyquinoline were obtained in the form of abeige-colored solid.

[3416] Mass spectrum: DCI m/z=176 MH⁺ base peak4-Hydroxy-6-methoxyquinoline-3-carboxylic acid can be prepared accordingto B. R. Baker and Ray R. Bramhall, J. Med. Chem. 15, 230 (1972).

EXAMPLE 24-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[3417] A mixture of 0.7 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)-ethyl]piperidine-4-carboxylatein 10 cm³ of aqueous 5M hydrochloric acid was stirred for 5 hours at atemperature in the region of 100° C. After cooling to about 20° C., thereaction mixture was concentrated to dryness under reduced pressure (5kPa) at a temperature in the region of 40° C. The residue obtained waspurified by chromatography under a nitrogen pressure of 100 kPa, on acolumn of silica gel (particle size 40-63μ; diameter 2.5 cm; height 35cm), eluting with a mixture of dichloromethane/methanol/28% aqueousammonia (89/10/1 by volume) and collecting 25-cm³ fractions. Fractions16 to 25 were collected.

[3418] These fractions were combined and then concentrated under theabove conditions. The evaporation residue obtained was slurried in 10cm³ of diisopropyl ether. The resulting crystalline product was filteredoff, washed with twice 5 cm³ of the same solvent and air-dried. 0.37 gof4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 204° C.

[3419]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) from 1.20 to 2.15(mt: 10H); 2,62 (t, J=5.5 Hz: 2H); from 2.65 to 2.80 (mt: 2H); 3.18 (mt:2H); 3.96 (s: 3H); 4.08 (t, J=5.5 Hz: 2H); from 6.60 to 6.85 (mt: 3H);7.38 (d, J=2.5 Hz: 1H); 7.46 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz:1H); 8.68 (s: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylate

[3420] A suspension composed of 1.36 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.95 g of 1-(2-bromoethoxy)-3,5-difluorobenzene (90% pure) and 0.5 g ofpotassium carbonate in 45 cm³ of acetonitrile was heated at atemperature in the region of 80° C. for 16 hours, with stirring andunder an inert atmosphere. After cooling to a temperature in the regionof 20° C., the reaction mixture was filtered and the insoluble materialwas washed with acetonitrile. The filtrate and the washing waters werecombined and concentrated under reduced pressure (5 kPa) at atemperature in the region of 40° C.

[3421] The evaporation residue was purified by chromatography under anitrogen pressure of 100 kPa, on a column of silica gel (particle size40-63μ; diameter 3.5 cm; height 45 cm), eluting with a mixture ofdichloromethane/methanol (97/3 by volume) and collecting 40-cm³fractions. Fractions 18 to 23 were collected. These fractions werecombined and then concentrated to dryness under reduced pressure (5 kPa)at a temperature in the region of 40° C. 1.56 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylatewere obtained in the form of an orange-colored oil.

[3422] Infra-red spectrum (CH₂Cl₂): 2955; 1723; 1622; 1599; 1229; 1153;1116 and 843 cm⁻¹.

[3423] Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewere prepared as described in Example 1.

EXAMPLE 34-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-cyclohexylethyl)piperidine-4-carboxylicacid

[3424] A mixture of 0.6 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-cyclohexylethyl)piperidine-4-carboxylate in 9.6 cm³ ofaqueous 5M hydrochloric acid was heated at a temperature in the regionof 100° C. with stirring for 5 hours.

[3425] The solution obtained was concentrated under reduced pressure (5kPa) at a temperature in the region of 40° C. The evaporation residueobtained was slurried in diisopropyl ether. The resulting crystallineproduct was filtered off, washed with the same solvent and oven-dried ata temperature in the region of 60° C., under reduced pressure (10 Pa). Asolid was obtained, which was purified by chromatography under anitrogen pressure of 100 kPa, on a column of silica gel (particle size40-63μ; diameter 2.5 cm; height 40 cm), eluting with a mixture ofdichloromethane/-methanol/32% aqueous ammonia (89/10/1 by volume), andcollecting 25-cm³ fractions. Fractions 16 to 25 were combined and thenconcentrated under reduced pressure (5 kPa) at a temperature in theregion of 40° C. A crystalline product was obtained, which was stirredin 5 cm³ of diisopropyl ether. The product obtained was filtered off,washed with the same solvent and air-dried. 0.33 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-cyclohexylethyl)piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 234° C.

[3426]¹H NMR spectrum (300 MHz, CD₃OD-d₄, δ in ppm) from 0.95 to2.20-2.42—from 2.90 to 3.15 and from 3.30 to 3.50 (respectively, mt,broad d, J=13.5 Hz, mt and mt: 29H in total); 4.11 (s: 3H); 7.52 (mt:2H); 8.02 (broad d, J=9 Hz: 1H); 8.68 (s: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-cyclohexylethyl)piperidine-4-carboxylate

[3427] 0.56 cm³ of 2-cyclohexylethyl bromide and 0.5 g of potassiumcarbonate were added, with stirring and under an inert atmosphere, at atemperature in the region of 20° C., to a solution of 1.36 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate in50 cm³ of acetonitrile. The suspension obtained was heated at about 80°C. for 16 hours and, after cooling to a temperature in the region of 20°C., the reaction mixture was filtered and concentrated to dryness underreduced pressure (5 kPa) at a temperature in the region of 40° C.

[3428] The residue obtained was purified by chromatography under anitrogen pressure of 100 kPa, on a column of silica gel (particle size40-63μ; diameter 3.5 cm; height 45 cm), eluting with a mixture ofdichloromethane/methanol (97/3 by volume) and collecting 40-cm³fractions. Fractions 22 to 30 were combined and concentrated to drynessunder reduced pressure (5 kPa) at a temperature in the region of 40° C.1.33 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-cyclohexylethyl)piperidine-4-carboxylatewere obtained in the form of an orange-colored oil.

[3429] Infra-red spectrum (CCl₄): 2925; 1727; 1622; 1503; 1230; 1116;833 and 697 cm⁻¹.

[3430] Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]piperidine-4-carboxylatewas prepared as described in Example 1.

EXAMPLE 4 b4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylicacid dihydrochloride

[3431] 0.5 g of benzyl4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-1-(3-phenylpropyl)-piperidine-4-carboxylatein 8 cm³ of 5M hydrochloric acid was heated at a temperature in theregion of 100° C., with stirring, for 5 hours. After cooling to about20° C., the reaction mass was concentrated under reduced pressure (5kPa) at a temperature in the region of 40° C.

[3432] The evaporation residue obtained was taken up in 6 cm³ of amixture of dichloromethane/methanol (90/10 by volume) and the mixturewas again concentrated to dryness under the above conditions. A foam wasobtained, which was slurried in 5 cm³ of diisopropyl ether. Thecrystalline product formed was filtered off, washed with three times 5cm³ of the same solvent and dried in an oven under reduced pressure (10Pa) at a temperature in the region of 50° C. 0.46 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylicacid dihydrochloride was obtained in the form of a beige-colored solid.

[3433]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.40 to2.25 and from 2.50 to 3.60 (mts: 20H in total); 3.96 (s: 3H); from 7.10to 7.45 (mt: 5H); 7.39 (d, J=2.5 Hz: 1H); 7.47 (dd, J=9 and 2.5 Hz: 1H);7.98 (d, J=9 Hz: 1H); 8.70 (s: 1H); 10.25 (broad multiplet: 1H).

Benzyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylate

[3434] A mixture composed of 1.36 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.55 cm³ of 1-bromo-3-phenylpropane and 0.5 g of potassium carbonate in45 cm³ of acetonitrile was heated with stirring and under an inertatmosphere for 16 hours at a temperature in the region of 80° C. Aftercooling, the reaction mixture was filtered and the insoluble materialwas then washed with acetonitrile. The filtrate was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3435] An oil was obtained, which was purified by chromatography under anitrogen pressure of 100 kPa, on a column of silica gel (particle size40-63μ; diameter 3.5 cm; height 30 cm), eluting with a mixture ofdichloromethane/-methanol (97/3 by volume) and collecting 40-cm³fractions. Fractions 21 to 25 were combined and then concentrated asabove. 21 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylatewere obtained in the form of an orange-colored viscous oil.

[3436] Infra-red spectrum (CH₂Cl₂) : 2948; 2812; 1722; 1622; 1504; 1229;1118; 1029 and 834 cm⁻¹.

[3437] Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 1.

EXAMPLE 54-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid trihydrochloride

[3438] A mixture of 0.4 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thio-ethyl]piperidine-4-carboxylatein 7 cm³ of aqueous 5M hydrochloric acid was maintained at a temperaturein the region of 100° C., with stirring and under an inert atmosphere,for 4 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 40° C.

[3439] The residue obtained was taken up in 10 cm³ of a mixture ofdichloromethane/methanol (90/10 by volume). The mixture was concentratedto dryness under the above conditions. 0.45 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyrid-2-yl)thioethyl]piperidine-4-carboxylicacid trihydrochloride was obtained in the form of a foam melting withdecomposition at 132° C.

[3440]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.59 (mt: 2H);from 1.65 to 1.95 (mt: 4H); 2.20 (broad d, J=13.5 Hz: 2H); 2.86 (mt:2H); from 3.10 to 3.65 (mt: 8H); 3.99 (s: 3H); 7.19 (broad dd, J=7,5 and4.5 Hz: 1H); from 7.35 to 7.50 (mt: 2H); 7.50 (dd, J=9 and 3 Hz: 1H);7.71 (resolved t, J=7,5 and 1.5 Hz: 1H); 8.01 (d, J=9 Hz: 1H); 8.48(broad d, J=4.5 Hz: 1H); 8.74 (s: 1H); 10.70 (multiplet: 1H).

Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-pyrid-2-yl)thioethyl]piperidine-4-carboxylate

[3441] Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2-pyrid-2-yl)thioethyl]piperidine-4-carboxylatewas prepared by analogy with the method described in Example 1, startingwith ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride.

[3442] Infra-red spectrum (CCl₄): 2955; 1726; 1622; 1580; 1503; 1414;1229; 1125; 1030 and 833 cm⁻¹.

Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride

[3443] A mixture of 2.6 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylatein 40 cm³ of dioxane, to which was added 14 cm³ of 4 N hydrochloricdioxane, was stirred for 16 hours at a temperature in the region of 20°C. The suspension obtained was diluted by addition of 100 cm³ of diethylether, stirred at about 20° C. for 1 hour and then filtered. The cakewas washed with twice 40 cm³ of diethyl ether and then dried in adesiccator under reduced pressure (5 kPa). 1.9 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewere obtained in the form of a white solid.

[3444] Infra-red spectrum (KBr): 2965; 2474; 1720; 1620; 1584; 1416;1241; 1119; 1019; 872 and 743 cm⁻¹.

Ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

[3445] 30 cm³ of a 0.5M solution of 9-borabicyclo-[3.3.1]nonane intetrahydrofuran were added to a solution of 2.96 g of ethyl4-allyl-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate in 30 cm³ oftetrahydrofuran, stirred at a temperature in the region of −10° C. underan inert atmosphere, while keeping the temperature below 0° C. After theaddition, the temperature of the mixture was brought to about 20° C. andthe mixture was then stirred for a further 4 hours. 3.1 g of4-bromo-3-chloro-6-methoxyquinoline were added, followed by 50 cm³ ofdioxane, 6.4 g of tribasic potassium phosphate and 0.22 g ofdiphenylphosphinoferrocene palladium chloride. The reaction mixture washeated at a temperature in the region of 50° C. for 16 hours. Aftercooling to a temperature in the region of 20° C., the mixture wasfiltered and the cake was then washed with 3 times 50 cm³ of ethylacetate. The filtrate was washed with 100 cm³ of water and then withtwice 50 cm³ of saturated aqueous sodium chloride solution. The organicphase was dried over magnesium sulfate, filtered and concentrated underreduced pressure (5 kPa), at a temperature in the region of 40° C.

[3446] A brown oil was obtained, which was purified by chromatography,under a pressure of 50 kPa of nitrogen, on a column of silica gel(particle size 20-45μ; diameter 4.5 cm; height 42 cm), eluting with amixture of cyclohexane/ethyl acetate (80/20 by volume). The fractionscontaining the expected product were collected. These fractions werecombined and then concentrated under reduced pressure (5 kPa) at atemperature in the region of 40° C. 2.62 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatewere obtained in the form of a yellow oil.

[3447] Infra-red spectrum: (CH₂Cl₂): 1720; 1682; 1622; 1504; 1423; 1367;1229; 1174; 1027 and 834 cm⁻¹.

[3448] Ethyl 4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylatewas prepared as described in Example 1.

EXAMPLE 6 Sodium salt of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylicacid

[3449] A mixture of 0.48 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylate in 7 cm³ of aqueous 5 Mhydrochloric acid was maintaied at a temperature in the region of 100°C., with stirring and under an inert atmosphere, for 6 hours. Aftercooling to about 20° C., the reaction mixture was stirred for 24 hoursand then evaporated under reduced pressure (5 kPa) at a temperature inthe region of 40° C. The residue obtained was purified by chromatographyunder a nitrogen pressure of 100 kPa, on a column of silica gel(particle size 40-60μ; diameter 2.5 cm, height 35 cm), eluting with amixture of dichloromethane/methanol/aqueous ammonia (84/15/1 by volume)and collecting 40-cm³ fractions. Fractions 19 to 24 were combined andthen concentrated as above. The solid obtained was stirred in 10 cm³ ofdiisopropyl ether, filtered and washed with 3 times 5 cm³ of diisopropylether. 0.35 g of the sodium salt of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylicacid was obtained in the form of a solid melting at 223° C.

[3450]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.87 (t, J=7 Hz:3H); from 1.10 to 1.45 (mt: 12H); from 1.45 to 1.70 (mt: 4H); from 1.85to 2.05 (mt: 2H); 1.97 (broad d, J=10.5 Hz: 2H); 2.17 (broad t, J=7.5Hz: 2H); from 2.45 to 2.60 (mt: 2H); 3.15 (mt: 2H); 3.97 (s: 3H); 7.40(mt: 1H); 7.44 (dd, J=9 and 3 Hz: 1H); 7.95 (d, J=9 Hz: 1H); 8.66 (s:1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylate

[3451] 1.36 g of benzyl4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]piperidine-4-carboxylateand 0.5 g of potassium carbonate were added, at a temperature in theregion of 20° C., with stirring and under an inert atmosphere, to asolution of 0.61 cm³ of 1-iodoheptane in 45 cm³ of acetonitrile. Afterheating for 18 hours at a temperature in the region of 80° C., a further1.17 cm³ of 1-iodoheptane were added. After heating for 40 hours at atemperature in the region of 80° C., the reaction mixture was cooled toabout 20° C., filtered and concentrated under reduced pressure (1 kPa)at a temperature in the region of 50° C.

[3452] The residue obtained was purified by chromatography under anitrogen pressure of 100 kPa, on a column of silica gel (particle size40-60μ; diameter 3.5 cm; height 35 cm), eluting with a mixture ofdichloromethane/methanol (95/05 by volume) and collecting 35-cm³fractions. Fractions 18 to 26 were combined and then concentrated asabove. 0.36 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylatewas obtained.

[3453] Infra-red spectrum (CH₂Cl₂): 2957; 2931; 1722; 1622; 1504; 1229;1159; 1118; 1028 and 834 cm⁻¹.

[3454] Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 1.

EXAMPLE 74-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid dihydrochloride

[3455] A mixture of 0.55 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]-piperidine-4-carboxylatein 8 cm³ of aqueous 6 N hydrochloric acid was heated at a temperature inthe region of 100° C., with stirring and under an inert atmosphere, for5 hours. After stirring for 18 hours at a temperature in the region of20° C., the solution obtained was concentrated under reduced pressure (5kPa) at a temperature in the region of 40° C. The evaporation residueobtained was taken up in 10 cm³ of a mixture of dichloromethane/methanol(90/10 by volume) and then concentrated under the same conditions asabove. 0.59 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylicacid dihydrochloride was obtained in the form of a foam melting at 129°C. with softening.

[3456]¹H NMR spectrum: (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.30 to2.10 (mt: 14H); 2.15 (broad d, J=13.5 Hz: 2H); from 2.65 to 3.00 (mt:4H); from 3.05 to 3.40 (mt: 5H); 3.46 (broad d, J=12 Hz: 2H); 3.97 (s:3H); 7.42 (d, J=2.5 Hz: 1H); 7.48 (dd, J=9 and 2.5 Hz: 1H); 7.99 (d, J=9Hz: 1H); 8.72 (s: 1H); from 10.55 to 10.90 (multiplet: 1H).

Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-carboxylate

[3457] 1.2 g of ethyl4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]piperidine-4-carboxylate,0.51 g of potassium carbonate and 0.61 g of potassium iodide were added,at a temperature in the region of 20° C., with stirring and under aninert atmosphere, to a solution of 0.607 g of(2-chloroethylthio)cyclopentane in 50 cm³ of acetonitrile. After heatingfor 20 hours at a temperature in the region of 80° C., the reactionmixture was cooled to about 20° C., filtered and concentrated underreduced pressure (1 kPa) at a temperature in the region of 50° C. Theresidue obtained was purified by chromatography under a nitrogenpressure of 100 kPa, on a column of silica gel (particle size 40-60μ;diameter 3.5 cm), eluting with a mixture of dichloromethane/methanol(98/2 by volume) and collecting 35-cm³ fractions. Fractions 25 to 31were combined and then concentrated as above. 0.9 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-(cyclopentylthio)ethyl]piperidine-4-carboxylatewas obtained.

[3458] Infra-red spectrum (CCl₄): 958; 1726; 1622; 1503; 1229; 1117;1030 and 833 cm⁻¹.

[3459] Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 5.

EXAMPLE 84-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thien-2-yl)thioethyl]piperidine-4-aceticacid

[3460] Working in a manner analogous to that of the preceding examples,4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thien-2-yl)thioethyl]piperidine-4-aceticacid was prepared.

[3461]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.30 to1.70 (mt: 8H); 2.14 (s: 2H); 2.33 (mt: 4H); from 2.45 to 2.60 (mt: 2H);2.92 (broad t, J=7 Hz: 2H); 3.13 (mt: 2H); 3.96 (s: 3H); 7.05 (dd, J=5.5and 3.5 Hz: 1H); 7.18 (dd, J=3.5 and 1 Hz: 1H); 7.39 (d, J=3 Hz: 1H);7.44 (dd, J=9 and 3 Hz: 1H); 7.60 (dd, J=5.5 and 1 Hz: 1H); 7.95 (d, J=9Hz: 1H); 8.66 (s: 1H).

EXAMPLE 9{4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-yl}methanol

[3462] Working in a manner analogous to that of the preceding examples,{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-4-yl}methanolwas prepared.

[3463]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) from 1.15 to 1.75(mt: 14H); 1.95 (mt: 2H); from 2.20 to 2.40 (mt: 4H); 2.44 (mt: 2H);2.57 (mt: 2H); from 3.05 to 3.25 (mt: 5H); 3.97 (s: 3H); 4.38 (t, J=5.5Hz: 1H); 7.38 (d, J=3 Hz: 1H); 7.45 (dd, J=9 and 3 Hz: 1H); 7.96 (d, J=9Hz: 1H); 8.68 (s: 1H).

EXAMPLE 104-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[(3-phenylpropyl)piperidine-4-yl]methanol

[3464] Working in a manner analogous to that of the preceding examples,4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[(3-phenylpropyl)piperidine-4-yl]methanolwas prepared.

[3465]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.59 (mt: 2H);from 1.65 to 1.95 (mt: 4H); 2.20 (broad d, J=13.5 Hz: 2H); 2.86 (mt:2H); from 3.10 to 3.65 (mt: 8H); 3.99 (s: 3H); 7.19 (broad dd, J=7.5 and4.5 Hz: 1H); from 7.35 to 7.50 (mt: 2H); 7.50 (dd, J=9 and 3 Hz: 1H);7.71 (resolved t, J=7.5 and 1.5 Hz: 1H); 8.01 (d, J=9 Hz: 1H); 8.48(broad d, J=4.5 Hz: 1H); 8.74 (s: 1H); 10.70 (multiplet: 1H).

EXAMPLE 114-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[3466] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]-piperidine-4-carboxylatein 5 cm³ of aqueous 5N hydrochloric acid and 3 cm³ of dioxane wasmaintained at a temperature in the region of 100° C. with stirring andunder an inert atmosphere for 20 hours. After cooling to about 20° C.,the reaction mixture was concentrated to dryness under reduced pressure(2 kPa) at a temperature in the region of 40° C. The mixture wasfiltered and then chromatographed, under atmospheric pressure, on acolumn of silica gel (particle size 40-63μ; diameter 1.5 cm; mass 55 g),eluting with a mixture of chloroform/methanol/aqueous ammonia (12/3/0.5by volume) and collecting 15-cm³ fractions. Fractions 5 to 12 werecombined and then concentrated to dryness under the above conditions.0.26 g of4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid was obtained in the form of a white crystalline solid melting at180° C.

[3467]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) 1.31 (very broadt), J=13 Hz: 2H); from 1.50 to 1.70 (mt: 4H); from 1.85 to 2.05 (mt:4H); 2.45 (broad t, J=7 Hz: 2H); 2.60 (broad d, J=11 Hz: 2H); 2.91(broad t, J=7 Hz: 2H); 3.04 (very broad t, J=6 Hz: 2H); 3.96 (s: 3H);7.04 (dd, J=5 and 3.5 Hz: 1H); 7.17 (dd, J=3.5 and 1 Hz: 1H); 7.35 (d,J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H); 7.60 (dd, J=5 and 1 Hz:1H); 7.97 (d, J=9 Hz: 1H); 8.70 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylate

[3468] A mixture of 0.8 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.6 g of 2-(2-bromoethylthio)thiophene and 1.5 g of potassium carbonatein 10 cm³ of acetonitrile was heated for 18 hours at a temperature inthe region of 80° C., with stirring and under an inert atmosphere. Aftercooling to a temperature in the region of 20° C., the reaction mixturewas concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C.

[3469] The residue obtained was taken up in dichloromethane and water.The organic phase was washed with water and a saturated sodium chloridesolution, dried over magnesium sulfate, filtered and concentrated todryness under the above conditions. The residue was purified bychromatography under atmospheric pressure, on a column of silica gel(particle size 70-200μ; diameter 3 cm; mass 50 g), eluting with amixture of ethyl acetate/petroleum ether (40-65° C.) (75/25 by volume)and collecting 30-cm³ fractions. Fractions 3 to 5 were combined and thenconcentrated to dryness under the above conditions. 0.7 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylatewas obtained in the form of a thick colorless oil.

[3470]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.99 (t, J=7 Hz:3H); 1.34 (very broad t, J=12 Hz: 2H); from 1.45 to 1.65 (mt: 4H); from1.85 to 2.00 (mt: 4H); 2.44 (broad t, J=7 Hz: 2H); 2.59 (broad d, J=11.5Hz: 2H); 2.89 (broad t, J=7 Hz: 2H); 3.03 (very broad t, J=6.5 Hz: 2H);3.94 (s: 3H); 3.96 (q, J=7 Hz: 2H); 7.02 (dd, J=5 and 3.5 Hz: 1H); 7.16(dd, J=3.5 and 1 Hz: 1H); 7.32 (d, J=2.5 Hz: 1H); 7.39 (dd, J=9 and 2.5Hz: 1H); 7.58 (dd, J=5 and 1 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.69 (broads: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3471] 2 cm³ of trifluoroacetic acid were added, with stirring and underan inert atmosphere, at a temperature in the region of 5° C., to asolution of 0.5 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatein 10 cm³ of dichloromethane. After 45 minutes, the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3472] The residue was taken up in diethyl ether and washed with asaturated potassium bicarbonate solution and then with a saturatedpotassium carbonate solution. The organic phase was washed with twice 5cm³ of water and then with a saturated sodium chloride solution, driedover magnesium sulfate, filtered and then concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. 0.26 gof ethyl4-(3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained in the form of a thick oil.

[3473]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) 1.02 (t, J=7 Hz:3H); 1.28 (mt: 2H); from 1.45 to 1.70 (mt: 4H); 1.90 (broad d, J=13.5Hz: 2H); 2.46 (broad t, J=12 Hz: 2H); 2.79 (d mt, J=12 Hz: 2H); 3.06(broad t, J=6 Hz: 2H); 3.95 (s: 3H); 3.98 (q, J=7 Hz: 2H); 7.35 (d,J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.70(d, J=1 Hz: 1H).

Ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

[3474] 1.4 g of ethyl4-allyl-1-(tert-butyloxy-carbonyl)piperidine-4-carboxylate were cooledto a temperature in the region of −30° C. and 11 cm³ of a 0.5 M solutionof 9-borabicyclo[3.3.1]nonane in tetrahydrofuran were added, withstirring and under an inert atmosphere. After the addition, thetemperature of the mixture was returned to about 20° C.

[3475] The solution obtained was stirred for a further 4 hours, followedby addition of 0.09 g of palladium diphenylphosphinoferrocene chloride,1.4 g of 4-iodo-3-fluoro-6-methoxyquinoline and 2.5 g of tribasicpotassium phosphate. After stirring for 16 hours at a temperature in theregion of 60° C., the reaction mixture was cooled to about 20° C. andthen concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. The residue obtained was taken up inethyl acetate and water, the phases were separated by settling and theorganic phase was dried over magnesium sulfate, filtered andconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3476] The residue obtained was purified by chromatography, underatmospheric pressure, on a column of silica gel (particle size 70-200μ;diameter 4.5 cm; mass 125 g), eluting with a mixture ofdichloromethane/ethyl acetate (98/2 by volume), and collecting 20-cm³fractions. Fractions 98 to 170 were combined and then concentrated todryness under the above conditions. 1.5 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatewere obtained in the form of a thick brown oil.

[3477]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.02 (t, J=7 Hz:3H); 1.30 (mt:2H); 1.39 (s: 9H); from 1.45 to 1.70 (mt: 4H); 1.92 (broadd, J=13.5 Hz: 2H); 2.81 (mt: 2H); 3.05 (broad t, J=6.5 Hz: 2H); 3.69(broad d, J=13.5 Hz: 2H); 3.95 (s: 3H); 4.00 (q, J=7 Hz: 2H); 7.34 (d,J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.70(d, J=1 Hz: 1H).

4-Iodo-3-fluoro-6-methoxyquinoline

[3478] 1.8 cm³ of diisopropylamine in 80 cm³ of tetrahydrofuran werecooled to a temperature in the region of −75° C. and 7.7 cm³ of a 1.6 Msolution of butyl lithium in hexane were added, with stirring and underan inert atmosphere. After stirring for 20 minutes at a temperature inthe region of −75° C., a solution of 2.2 g of3-fluoro-6-methoxyquinoline in 20 cm³ of tetrahydrofuran was added. Thesolution obtained was stirred for a further 4 hours, followed byaddition of a solution of 3.3 g of double-sublimated iodine in 10 cm³ oftetrahydrofuran. After stirring for 2 hours at a temperature in theregion of 20° C., the reaction mixture was hydrolyzed with 200 cm³ of a90/10 tetrahydrofuran/water mixture and then 100 cm³ of a saturatedsodium chloride solution and 150 cm³ of ethyl acetate. The mixture waswashed with 3 times 80 cm³ of a saturated sodium chloride solution,dried over magnesium sulfate, filtered and concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C.

[3479] The residue obtained was purified by chromatography, underatmospheric pressure, on a column of silica gel (particle size 70-200μ;diameter 5 cm; height 35 cm), eluting with a mixture of 90/10 petroleumether/ethyl acetate. Fractions 66 to 95 were combined and thenconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 40° C. 0.9 g of 4-iodo-3-fluoro-6-methoxyquinoline wasobtained in the form of a cream-colored solid.

[3480]¹H NMR Spectrum (300 MHz, (CD₃)2SO-d₆, δ in ppm): 4.00 (s: 3H);7.31 (d, J 2.5 Hz: 1H); 7.47 (dd, J=9 and 2.5 Hz: 1H); 8.01 (d, J=9 Hz:1H); 8.64 (s: 1H).

3-Fluoro-6-methoxyquinoline

[3481] A mixture of 1.35 g of 4-chloro-3-fluoro-6-methoxyquinoline, 1.1cm³ of triethylamine and 100 mg of palladium-on-charcoal in 23 cm³ ofmethanol was stirred at a temperature in the region of 20° C. under apressure of 2 bar of hydrogen for 18 hours. The reaction mixture wasfiltered and then concentrated to dryness under reduced pressure (2 kPa)at a temperature in the region of 40° C.

[3482] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 70-200μ;diameter 3 cm; mass 40 g), eluting with dichloromethane/ethyl acetate(95/5 by volume). The fractions containing the product were combined andthen concentrated to dryness according to the above conditions. 1 g of3-fluoro-6-methoxyquinoline was obtained.

[3483]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) 3.92 (s: 3H);7.40 (mt: 2H); 8.07 (d, J=9 Hz: 1H); 8.04 (dd, J=10 and 3 Hz: 1H); 8.77(d, J=3 Hz: 1H).

4-Chloro-3-fluoro-6-methoxyquinoline

[3484] 1.3 cm³ of diisopropylamine in 50 cm³ of tetrahydrofuran werecooled to a temperature in the region of −75° C. and 5.8 cm³ of a 1.6 Msolution of butyl lithium in hexane were added, with stirring and underan inert atmosphere. After stirring for 20 minutes at a temperature inthe region of −75° C., a solution of 1.2 g of4-chloro-6-methoxyquinoline in 20 cm³ of tetrahydrofuran was added. Thesolution obtained was stirred for a further 4 hours, followed byaddition of a solution of 2.9 g of N-fluorobenzene sulfonimide in 10 cm³of tetrahydrofuran. After stirring for 2 hours at a temperature in theregion of 20° C., the reaction mixture was hydrolyzed with 200 cm³ of a90/10 tetrahydrofuran/water mixture and then 100 cm³ of a saturatedsodium chloride solution and 150 cm³ of ethyl acetate. The mixture waswashed with 3 times 80 cm³ of a saturated sodium chloride solution,dried over magnesium sulfate, filtered and concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C.

[3485] The residue obtained was purified by chromatography, underatmospheric pressure, on a column of silica gel (particle size 70-200μ;diameter 4 cm; mass 100 g), eluting with dichloromethane. The fractionscontaining the product were combined and then concentrated to drynessunder reduced pressure (5 kPa) at a temperature in the region of 40° C.0.4 g of 4-chloro-3-fluoro-6-methoxyquinoline was obtained.

[3486]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 4.01 (s: 3H);7.43 (d, J=2.5 Hz: 1H); 7.52 (dd, J=9 and 2.5 Hz: 1H); 8.07 (d, J=9 Hz:1H); 8.91 (d, J=1 Hz: 1H).

4-Chloro-6-methoxyquinoline

[3487] A mixture of 12 g of 4-hydroxy-6-methoxy-quinoline in 50 cm ³ ofphosphorus oxychloride was maintained at a temperature in the region of100° C., with stirring and under an inert atmosphere, for 2 hours. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of40° C. and then hydrolyzed with ice and brought to pH=10 using a 5 Nsodium hydroxide solution. The mixture was extracted with ethyl acetate,dried over magnesium sulfate, filtered and concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C.

[3488] The residue obtained was chromatographed, under atmosphericpressure, on a column of silica gel (particle size 70-200μ), elutingwith a mixture of dichloromethane/methanol (85/15 by volume). Thefractions containing the product were combined and then concentrated todryness according to the above conditions. 12 g of4-chloro-6-methoxyquinoline were obtained in the form of a white solidmelting at 82° C.

[3489]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) 3.958 (s: 3H);7.45 (d, J=2.5 Hz: 1H); 7.53 (dd, J=9 and 2.5 Hz: 1H); 7.76 (d, J=4.5Hz: 1H); 8.04 (d, J=9 Hz: 1H); 8.70 (d, J=4.5 Hz: 1H).

[3490] The ethyl4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate was preparedas described in Example 1.

[3491] The 4-hydroxy-6-methoxyquinoline was prepared as described inExample 1.

EXAMPLE 124-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-6-phenoxy)ethyl]piperidine-4-carboxylicacid

[3492] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-6-phenoxy)ethyl]piperidine-4-carboxylatein 6 cm³ of aqueous 5N hydrochloric acid and 10 cm³ of dioxane wasmaintained at a temperature in the region of 100° C., with stirring andunder an inert atmosphere, for 20 hours. After cooling to about 20° C.,the reaction mixture was concentrated to dryness under reduced pressure(2 kPa) at a temperature in the region of 40° C.

[3493] The residue obtained was chromatographed, at atmosphericpressure, on a column of silica gel (particle size 70-200μ; diameter 1.5cm; mass 50 g), eluting with a mixture of chloroform/methanol/aqueousammonia (12/3/0.5 by volume) and collecting 15-cm³ fractions. Fractions10 to 15 were combined and then concentrated to dryness according to theabove conditions. 0.2 g of4-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-2-(3,5-difluoro-6-phenoxy)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 175° C.

[3494]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.33 (very broadt, J=13 Hz: 2H); from 1.50 to 1.70 (mt: 4H); 1.95 (broad d, J=13 Hz:2H); 2.05 (broad t, J=11.5 Hz: 2H); 2.60 (t, J=6 Hz: 2H); 2.69 (broad d,J=11.5 Hz: 2H); 3.04 (mt: 2H); 3.96 (s: 3H); 4.06 (t, J=6 Hz: 2H); from6.65 to 6.85 (mt: 3H); 7.34 (d, J=2.5 Hz: 1H); 7.39 (dd, J=9 and 2.5 Hz:1H); 7.96 (d, J=9 Hz: 1H); 8.69 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-6-phenoxy)ethyl]piperidine-4-carboxylate

[3495] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.3 g of 1-(2-bromoethoxy)-3,5-difluorobenzene, 0.18 g of potassiumiodide and 0.74 g of potassium carbonate in 10 cm³ of acetonitrile washeated for 18 hours at a temperature in the region of 75° C., withstirring and under an inert atmosphere. After cooling to a temperaturein the region of 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3496] The residue obtained was taken up in ethyl acetate and water. Theorganic phase was washed with water and a saturated sodium chloridesolution, dried over magnesium sulfate, filtered and concentrated todryness under the above conditions. The residue was purified bychromatography, under atmospheric pressure, on a column of silica gel(particle size 70-200μ; diameter 1.5 cm; mass 35 g), eluting withdichloromethane. Fractions 7 to 11 were combined and then concentratedto dryness according to the above conditions. 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-6-phenoxy)ethyl]piperidine-4-carboxylatewas obtained in the form of a thick colorless oil.

[3497]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.00 (t, J=7 Hz:3H); 1.38 (very broad t, J=12 Hz: 2H); from 1.45 to 1.70 (mt: 4H); from1.90 to 2.10 (mt: 4H); 2.60 (t, J=6 Hz: 2H); 2.69 (very broad d, J=12Hz: 2H); 3.05 (very broad t, J=6.5 Hz: 2H); 3.95 (s: 3H); 3.98 (q, J=7Hz: 2H); 4.06 (t, J=6 Hz: 2H); from 6.65 to 6.85 (mt: 3H); 7.34 (d,J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.70(broad s: 1H).

[3498] The ethyl4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate was preparedas described in Example 1.

[3499] The 1-(2-bromoethoxy)-3,5-difluorobenzene may be obtained byapplying the method described in Example 16.

EXAMPLE 134-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-6-phenoxy)ethyl]piperidine-4-carboxylicacid dihydrochloride

[3500] A mixture of 1 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-6-phenoxy)ethyl]piperidine-4-carboxylate in 50 cm³ ofaqueous 5N hydrochloric acid was maintained at a temperature in theregion of 100° C. with stirring for 20 hours. After cooling to about 20°C., the reaction mixture was concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C.

[3501] The residue obtained was taken up in 50 cm³ of acetone, filtered,washed with 3 times 15 cm³ of [lacuna] and then dried in a desiccatorunder reduced pressure (0.1 kPa) at a temperature in the region of 40°C. 0.88 g of 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-6-phenoxy)ethyl]piperidine-4-carboxylic acid dihydrochloridewas obtained in the form of a white solid melting at 170° C.

[3502]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.45 to2.30 (mt:8H); from 2.85 to 3.70 (mt: 8H); 3.97 (s: 3H); 4.50 (mt: 2H);7.15 (mt: 2H); 7.40 (d, J=3 Hz: 1H); 7.46 (dd, J=9 and 3 Hz: 1H); 7.97(d, J=9 Hz: 1H); 8.69 (s: 1H); 10.07 (unresolved peak: 1H); from 12.50to 13.10 (broad unresolved peak: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-6-phenoxy)ethyl]piperidine-4-carboxylate

[3503] A mixture of 1.4 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride, 0.9 g of 1-(2-bromoethoxy)-2,3,5-tri-fluorobenzene, 0.6 gof potassium iodide and 2 g of potassium carbonate in 100 cm³ ofacetonitrile was heated for 18 hours at a temperature in the region of75° C. with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was filteredand washed with 3 times 30 cm³ of acetonitrile. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was purified bychromatography under atmospheric pressure, on a column of silica gel(particle size 20-45μ; diameter 3 cm; height: 27 cm), eluting with ethylacetate and collecting 50-cm³ fractions. Fractions 9 to 23 were combinedand then concentrated to dryness according to the above conditions. 1.27g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-6-phenoxy)ethyl]piperidine-4-carboxylatewere obtained in the form of a thick yellow oil.

[3504]¹H NMR Spectrum (300 MHz, (CD₃)2SO-d₆, δ in ppm): from 1.30 to1.60 (mt: 4H); 1.72 (mt: 2H); from 1.95 to 2.15 (mt: 4H); 2.64 (t, J=5.5Hz: 2H); 2.71 (DMF, J=12 Hz: 2H); 3.13 (broad t, J=7.5 Hz: 2H); 3.93 (s:3H); 4.16 (t, J=5.5 Hz: 2H); 5.04 (s: 2H); from 6.95 to 7.15 (mt: 2H);from 7.20 to 7.30 (mt: 5H); 7.34 (d, J=3 Hz: 1H); 7.45 (dd, J=9 and 3Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.67 (s: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride

[3505] A mixture of 17.4 g of benzyl1-tert-butyloxycarbonyl-4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatein 75 cm³ of 5N hydrochloric acid dissolved in dioxane and 200 cm³ ofdioxane was stirred at a temperature in the region of 20° C. for 20hours. 200 cm³ of diethyl ether were added to the reaction mixture. Theprecipitate formed was filtered off to give 14.26 g of benzyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride.

[3506]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.49 (mt: 2H);from 1.65 to 1.85 (mt: 4H); 2.11 (DMF , J=14 Hz: 2H); 2.78 (mt: 2H);from 3.10 to 3.25 (mt: 2H); 3.20 (broad t, J=7.5 Hz: 2H); 3.96 (s: 3H);5.09 (s: 2H); 7.28 (mt: 5H); 7.43 (d, J=3 Hz: 1H); 7.53 (dd, J=9 and 3Hz: 1H); 8.06 (d, J=9 Hz: 1H); 8.80 (s: 1H); from 9.05 to 9.30(unresolved peak: 2H).

1-(2-Bromoethoxy)-2,3,5-trifluorobenzene

[3507] A mixture of 11.4 g of 2,3,5-trifluorophenol, 40.5 cm³ of1,2-dibromoethane and 15.3 g of potassium carbonate in 200 cm³ ofacetonitrile was heated for 18 hours at a temperature in the region of75° C., with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was filteredand washed with 4 times 50 cm ³ of acetonitrile. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was taken up in 150 cm³ ofpetroleum ether (40-65° C.), filtered and washed with 3 times 30 cm³ ofpetroleum ether (40-65° C.). The filtrate was concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.

[3508] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 5 cm; height: 33 cm), eluting with petroleum ether (40-65° C.)and collecting 100-cm³ fractions. Fractions 28 to 63 were combined andthen concentrated to dryness according to the above conditions. 16.15 gof 1-(2-bromoethoxy)-2,3,5-trifluorobenzene were obtained in the form ofa thick colorless oil.

[3509]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) 3.83 (broad t,J=5.5 Hz: 2H); 4.45 (broad t, J=5.5 Hz: 2H); from 7.00 to 7.15 (mt: 2H).

[3510] The benzyl4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate was preparedas described in Example 1.

EXAMPLE 144-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluoro-6-phenylthio)ethyl]piperidine-4-carboxylic acid

[3511] A mixture of 1.3 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluoro-6-piperidine-4-carboxylate in 15 cm³ ofaqueous 5N hydrochloric acid and 15 cm³ of dioxane was maintained at atemperature in the region of 100° C. with stirring and under an inertatmosphere for 20 hours. After cooling to about 20° C., the reactionmixture was evaporated under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3512] The residue obtained was taken up 4 times in toluene, evaporatingbetween each washing. The oil obtained was taken up in achloroform/methanol/aqueous ammonia mixture (12/3/0.5 by volume), thephases were separated by settling and the organic phase was washed withwater and then left to crystallize for 20 hours. The solid obtained wasfiltered off and then dried in a desiccator under reduced pressure (0.1kPa) at a temperature in the region of 40° C. 0.6 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluoro-6-phenylthio)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white crystalline solid melting at205° C.

[3513]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆, δ in ppm) 1.39 (unresolvedpeak: 2H); 1.55 (mt: 2H); 1.70 (mt: 2H); from 1.90 to 2.20 (mt: 4H);from 2.40 to 2.85 (broad unresolved peak: 4H); from 3.05 to 3.25 (mt:2H); 3.17 (broad t, J=7.5 Hz: 2H); 3.96 (s: 3H); 7.07 (mt: 1H); 7.26(mt: 1H); 7.33 (mt: 1H); 7.38 (d, J=2.5 Hz: 1H); 7.46 (dd, J=9 and 2.5Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.68 (s: 1H); from 12.00 to 12.50(unresolved peak: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,5-difluoro-6-phenylthio)ethyl]piperidine-4-carboxylate

[3514] A mixture of 1.4 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.9 g of 1-(2-bromoethylthio)-2,5-difluorobenzene, 0.6 g of potassiumiodide and 2 g of potassium carbonate in 100 cm³ of acetonitrile washeated for 18 hours at a temperature in the region of 75° C., withstirring and under an inert atmosphere. After cooling to a temperaturein the region of 20° C., the reaction mixture was concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of40° C. The residue obtained was taken up in water and extracted withethyl acetate. The organic phase was washed with saturated sodiumchloride solution, dried over magnesium sulfate and then concentrated todryness as above.

[3515] The residue obtained was purified by chromatography, underatmospheric pressure, on a column of silica gel (particle size 70-200μ;diameter 2.5 cm; mass: 50 g), eluting with a mixture of ethyl acetateand dichloromethane (05/95 by volume) and collecting 15-cm³ fractions.Fractions 21 to 100 were combined and then concentrated to drynessaccording to the above conditions. 1.35 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,5-difluoro-6-phenylthio)-ethyl]-piperidine-4-carboxylatewere obtained in the form of a white solid melting at 95° C.

[3516]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.30 to1.60 (mt: 4H); 1.71 (mt: 2H); from 1.85 to 2.05 (mt: 4H); from 2.40 to2.60 (mt: 2H); 2.66 (DMF, J=12 Hz: 2H); from 3.05 to 3.20 (mt: 2H); 3.11(broad t, J=7.5 Hz: 2H); 3.92 (s: 3H); 5.03 (s: 2H); 7.04 (mt: 1H); from7.15 to 7.35 (mt: 7H); 7.35 (d, J=3 Hz: 1H); 7.44 (dd, J=9 and 3 Hz:1H); 7.95 (d, J=9 Hz: 1H); 8.66 (s: 1H).

1-(2-Bromoethylthio)-2,5-difluorobenzene

[3517] A mixture of 5.8 g of S-(2,5)-difluorophenyl-dimethylthiocarbamate in 80 cm³ of a 10% solution of potassium hydroxide inmethanol was heated for 1 hour at a temperature in the region of 100° C.with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3518] The residue obtained was taken up in water, extracted withdiethyl ether and then acidified with 40 cm³ of 5N hydrochloric acid.The aqueous phase was extracted with twice 30 cm³ of diethyl ether. Theorganic phases were combined, washed with saturated sodium chloridesolution, dried over sodium sulfate, filtered and then concentrated todryness as above. The residue obtained was taken up in 30 cm³ of1,2-dibromoethane and 0.5 g of aliquat 336, followed by addition of 20cm³ of cold sodium hydroxide solution. The solution obtained was stirredfor a further 18 hours at a temperature in the region of 20° C. and thenwashed with twice 15 cm³ of water. The organic phases were combined,washed with saturated sodium chloride solution, dried over sodiumsulfate, filtered and then concentrated to dryness as above.

[3519] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 70-200μ;diameter 2.5 cm; mass: 75 g), eluting with petroleum ether andcollecting 50-cm³ fractions. Fractions 4 to 13 were combined and thenconcentrated to dryness according to the above conditions. 4.4 g of1-(2-bromoethylthio)-2,5-difluorobenzene were obtained in the form of acolorless fluid oil.

[3520]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 3.50 (mt: 2H);3.66 (mt: 2H); 7.15 (mt: 1H); 7.32 (doubled triplet, J=9 and 4.5 Hz:1H); 7.42 (ddd, J=9-6.5 and 3 Hz: 1H).

Dimethyl S-(2,5)-difluorophenylthiocarbamate

[3521] 2 g of dimethyl O-(2,5)-difluorophenylthio-carbamate were heatedat a temperature in the region of 235° C. for 40 minutes. The residueobtained was purified by chromatography under atmospheric pressure, on acolumn of silica gel (particle size 70-200μ; diameter 3 cm; mass: 25 g),eluting with a mixture of petroleum ether and dichloromethane (50/50 byvolume) and collecting 15-cm³ fractions. Fractions 6 to 11 were combinedand then concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. 1.25 g of dimethylS-(2,5)-difluorophenylthiocarbamate were obtained in the form of a whitesolid melting at 96° C.

[3522]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 2.96 (unresolvedpeak: 3H); 3.08 (unresolved peak: 3H); from 7.35 to 7.50 (mt: 3H).

Dimethyl O-(2,5)-difluorophenylthiocarbamate

[3523] 14.1 g of dimethylthiocarbamate chloride and 13 g of1,4-diaza[2.2.2]tricyclooctane were added with stirring to a solution of7.5 g of 2,5-difluorophenol in 120 cm³ of dimethylformamide. Afterstirring for 1 hour at a temperature in the region of 20° C., thereaction mixture was taken up in 1 cm³ of water and 100 cm³ of dryconcentrated hydrochloric acid, and extracted with 400 cm³ of diethylether. The organic phase was dried over sodium sulfate, filtered andthen concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. The residue obtained was purified bychromatography under atmospheric pressure, on a column of silica gel(particle size 70-200μ; diameter 10 cm; mass: 400 g), eluting with amixture of petroleum ether and dichloromethane (50/50 by volume). Thefractions containing the expected product were combined and thenconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 40° C. 12.4 g of dimethylO-(2,5)-difluoropehnylthiocarbamate were obtained in the form of a solidmelting at 62° C.

[3524]¹H NMR Spectrum (300 MHz, (CD₃)2SO-d₆, δ in ppm) 3.35 (s: 3H);3.40 (s: 3H); from 7.15 to 7.30 (mt: 2H); 7.42 (doubled triplet, J=9.5and 5.5 Hz: 1H).

[3525] The benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride was prepared as described in Example 13.

EXAMPLE 154-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenoxy)ethyl]piperidine-4-carboxylicacid dihydrochloride

[3526] A mixture of 1 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenoxy)-ethyl]piperidine-4-carboxylatein 50 cm³ of aqueous 5N hydrochloric acid was maintained at atemperature in the region of 100° C., with stirring and under an inertatmosphere for 20 hours. After cooling to about 20° C., the reactionmixture was concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C.

[3527] The residue obtained was taken up in 50 cm³ of acetone and thenstirred for 1 hour at a temperature in the region of 20° C. The mixturewas filtered, washed with 3 times 15 cm³ of acetone and then dried in adesiccator under reduced pressure (0.1 kPa) at a temperature in theregion of 40° C. 0.86 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenoxy)ethyl]piperidine-4-carboxylicacid dihydrochloride was obtained in the form of a white solid meltingat 218° C.

[3528]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) 1.59 (mt: 2H);1.75 (mt: 2H); 1.82 (very broad t, J=14 Hz: 2H); 2.22 (broad d, J=14 Hz:2H); 2.98 (mt: 2H); 3.22 (broad t, J=7.5 Hz: 2H); from 3.45 to 3.70 (mt:4H); 3.98 (s: 3H); 4.51 (t, J=5 Hz: 2H); from 7.15 to 7.25 (mt: 3H);7.42 (d, J=3 Hz: 1H); 7.48 (dd, J=9 and 3 Hz: 1H); 7.99 (d, J=9 Hz: 1H);8.72 (s: 1H); 10.66 (unresolved peak: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenoxy)ethyl]piperidine-4-carboxylate

[3529] A mixture of 1.4 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.82 g of 1-(2-bromoethoxy)-2,6-difluorobenzene, 0.6 g of potassiumiodide and 2 g of potassium carbonate in 100 cm³ of acetonitrile washeated for 18 hours at a temperature in the region of 75° C., withstirring and under an inert atmosphere. After cooling to a temperaturein the region of 20° C., the reaction mixture was filtered and washedwith three times 30 cm³ of acetonitrile. The filtrate was concentratedto dryness under reduced pressure (2 kPa) at a temperature in the regionof 40° C. The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 3 cm; height: 27 cm), eluting with ethyl acetate and collecting50-cm³ fractions. Fractions 7 to 17 were combined and then concentratedto dryness under the above conditions. 1.65 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,6-difluorophenoxy)ethyl]piperidine-4-carboxylatewere obtained in the form of a thick yellow oil.

[3530]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.25 to1.55 (mt: 4H); 1.70 (mt: 2H); from 1.90 to 2.10 (mt: 4H); 2.59 (t, J=6Hz: 2H); 2.66 (DMF, J=12 Hz: 2H); 3.13 (broad t, J=7.5 Hz: 2H); 3.93 (s:3H); 4.14 (t, J=6 Hz: 2H); 5.03 (s: 2H); from 7.05 to 7.20 (mt: 3H);7.35 (mt: 5H); 7.35 (d, J=3 Hz: 1H); 7.46 (dd, J=9 and 3 Hz: 1H); 7.97(d, J=9 Hz: 1H); 8.67 (s: 1H).

1-(2-Bromoethoxy)-2,6-difluorobenzene

[3531] A mixture of 10 g of 2,6-difluorophenol, 40.5 cm³ of1,2-dibromoethane and 15.3 g of potassium carbonate in 300 cm³ ofacetonitrile was heated for 18 hours at a temperature in the region of75° C., with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was filteredand washed with 3 times 30 cm³ of acetonitrile. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was taken up in 200 cm³ ofpetroleum ether (40-65° C.), filtered and washed with 3 times 30 cm³ ofpetroleum ether (40-65° C.). The filtrate was concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.The residue obtained was purified by chromatography under atmosphericpressure, on a column of silica gel (particle size 20-45μ; diameter 7cm; height: 28 cm), eluting with petroleum ether (40-65° C.) andcollecting 100-cm3 fractions. Fractions 22 to 58 were combined and thenconcentrated to dryness under the above conditions. 14.5 g of1-(2-bromoethoxy)-2,6-difluorobenzene were obtained in the form of athick colorless oil.

[3532]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 3.76 (broad t,J=6 Hz: 2H); 4.42 (broad t, J=6 Hz: 2H); from 7.10 to 7.25 (mt: 3H).

[3533] The benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride was prepared as described in Example 13.

EXAMPLE 164-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid dihydrochloride

[3534] A mixture of 1 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylatein 50 cm³ of 5N hydrochloric acid was maintained at a temperature in theregion of 100° C., with stirring and under an inert atmosphere for 20hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3535] The residue obtained was taken up in 50 cm³ of acetone and thenstirred for 1 hour at a temperature in the region of 20° C. The mixturewas filtered, washed with 3 times 15 cm³ of acetone and then dried in adesiccator under reduced pressure (0.1 kPa) at a temperature in theregion of 40° C. 0.8 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)-ethyl]piperidine-4-carboxylicacid dihydrochloride was obtained in the form of a white solid meltingat 180° C.

[3536]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.58 (mt: 2H);1.72 (mt: 2H); 1.84 (very broad t, J=14 Hz: 2H); 2.19 (broad d, J=14 Hz:2H); 2.95 (mt: 2H); 3.22 (broad t, J=7.5 Hz: 2H); 3.53 (mt: 4H); 3.98(s: 3H); 4.52 (t, J=5 Hz: 2H); 6.84 (mt: 1H); 7.22 (ddd, J=9-7 and 3 Hz:1H); 7.30 (ddd, J=10.5-9 and 4.5 Hz: 1H); 7.42 (d, J=2.5 Hz: 1H); 7.49(dd, J=9 and 2.5 Hz: 1H); 8.00 (d, J=9 Hz: 1H); 8.74 (s: 1H); 10.97(unresolved peak: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylate

[3537] A mixture of 1.4 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride, 0.82 g of 1-(2-bromoethoxy)-2,5-difluoro-benzene, 0.6 gof potassium iodide and 2 g of potassium carbonate in 100 cm³ ofacetonitrile was heated for 18 hours at a temperature in the region of75° C. with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was filteredand washed with 3 times 30 cm³ of acetonitrile. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3538] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 2.4 cm; height: 26 cm), eluting with ethyl acetate andcollecting 30-cm³ fractions. Fractions 7 to 14 were combined and thenconcentrated to dryness under the above conditions. 1.6 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylatewere obtained in the form of a thick yellow oil.

[3539]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.35 to1.60 (mt: 4H); 1.73 (mt: 2H); from 1.95 to 2.15 (mt: 4H); 2.63 (t, J=5.5Hz: 2H); 2.72 (DMF, J=12 Hz: 2H); 3.14 (broad t, J=7.5 Hz: 2H); 3.92 (s:3H); 4.12 (t, J=5.5 Hz: 2H); 5.04 (s: 2H); 6.75 (tripled triplet, J=9and 3 Hz: 1H); 7.13 (ddd, J=10.5-7.5 and 3 Hz: 1H); from 7.20 to 7.30(mt: 6H); 7.34 (d, J=3 Hz: 1H); 7.45 (dd, J=9 and 3 Hz: 1H); 7.97 (d,J=9 Hz: 1H); 8.67 (s: 1H).

1-(2-Bromoethoxy)-2,5-difluorobenzene

[3540] A mixture of 10 g of 2,5-difluorophenol, 40.5 cm³ of1,2-dibromoethane and 15.3 g of potassium carbonate in 200 cm³ ofacetonitrile was heated for 18 hours at a temperature in the region of75° C., with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was filteredand washed with 4 times 50 cm³ of acetonitrile. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was taken up in 150 cm³ ofpetroleum ether (40-65° C.), filtered and washed with 3 times 30 cm³ ofpetroleum ether (40-65°). The filtrate was concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C.

[3541] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 7 cm; height: 49 cm), eluting with petroleum ether (40-65° C.)and collecting 100-cm³ fractions. Fractions 29 to 88 were combined andthen concentrated to dryness under the above conditions. 13.5 g of1-(2-bromoethoxy)-2,5-difluorobenzene were obtained in the form of acolorless fluid oil.

[3542]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) 3.85 (broad t,J=6 Hz: 2H); 4.44 (broad t, J=6 Hz: 2H); 6.82 (mt: 1H); 7.18 (ddd, J=9-7and 3 Hz: 1H); 7.29 (ddd, J=11-9 and 5 Hz: 1H).

[3543] The benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride was prepared as described in Example 13.

EXAMPLE 174-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenoxy)ethyl]piperidine-4-carboxylicacid dihydrochloride

[3544] A mixture of 1 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenoxy)-ethyl]piperidine-4-carboxylatein 50 cm³ of aqueous 5N hydrochloric acid was maintained at atemperature in the region of 100° C., with stirring and under an inertatmosphere for 20 hours. After cooling to about 20° C., the reactionmixture was concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C.

[3545] The residue obtained was taken up in 50 cm³ of acetone and thenstirred for 1 hour at a temperature in the region of 20° C. The mixturewas filtered, washed with 3 times 15 cm³ of acetone and then dried in adesiccator under reduced pressure (0.1 kPa) at a temperature in theregion of 40° C. 0.9 g of4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,3-difluorophenoxy)-ethyl]piperidine-4-carboxylicacid dihydrochloride was obtained in the form of a white solid meltingat 259° C.

[3546]¹H NMR Spectrum (400 MHz (CD₃)₂SO-d₆, δ in ppm): from 1.45 to 1.65(mt: 2H); 1.73 (mt: 2H); 1.81 (very broad t, J=14 Hz: 2H); 2.20 (broadd, J=14 Hz: 2H); 2.97 (mt: 2H); 3.22 (broad t, J=7.5 Hz: 2H); from 3.45to 3.60 (mt: 4H); 3.98 (s: 3H); 4.54 (t, J=5 Hz: 2H); 7.09 (mt: 2H);7.20 (mt: 1H); 7.42 (d, J=2.5 Hz: 1H); 7.48 (dd, J=9 and 2.5 Hz: 1H);7.99 (d, J=9 Hz: 1H); 8.72 (s: 1H); 10.70 (unresolved peak: 1H); from12.40 to 13.30 (broad unresolved peak: 1H).

Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenoxy)ethyl]piperidine-4-carboxylate

[3547] A mixture of 1.4 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride, 0.82 g of 1-(2-bromoethoxy)-2,3-difluoro-benzene, 0.6 gof potassium iodide and 2 g of potassium carbonate in 100 cm³ ofacetonitrile was heated for 18 hours at a temperature in the region of75° C., with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was filteredand washed with 3 times 30 cm³ of acetonitrile. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3548] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 2.7 cm; height: 32 cm), eluting with ethyl acetate andcollecting 30-cm³ fractions. Fractions 7 to 21 were combined and thenconcentrated to dryness under the above conditions. 1.6 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3-difluorophenoxy)ethyl]piperidine-4-carboxylatewere obtained in the form of a thick yellow oil.

[3549]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) from 1.35 to 1.55(mt: 4H); 1.72 (mt: 2H); from 1.95 to 2.15 (mt: 4H); 2.64 (t, J=6 Hz:2H); 2.72 (DMF, J=12 Hz: 2H); 3.13 (broad t, J=7.5 Hz: 2H); 3.93 (s:3H); 4.15 (t, J=6 Hz: 2H); 5.04 (s: 2H); from 6.90 to 7.20 (mts: 3H);7.25 (mt: 5H); 7.35 (d, J=3 Hz: 1H); 7.46 (dd, J=9 and 3 Hz: 1H); 7.97(d, J=9 Hz; 1H); 8.67 (s: 1H).

1-(2-Bromoethoxy)-2,3-difluorobenzene

[3550] A mixture of 10 g of 2,3-difluorophenol, 40.5 cm³ of1,2-dibromoethane and 15.3 g of potassium carbonate in 200 cm³ ofacetonitrile was heated for 48 hours at a temperature in the region of75° C., with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was filteredand washed with 6 times 30 cm³ of acetonitrile. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3551] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 7 cm; height: 42 cm), eluting with a mixture of dichloromethaneand ethyl acetate (90/10 by volume) and collecting 100-cm³ fractions.Fractions 4 to 10 were combined and then concentrated to dryness underthe above conditions. The residue obtained was purified bychromatography under atmospheric pressure, on a column of silica gel(particle size 20-45μ; diameter 5 cm; height: 30 cm), eluting withpetroleum ether (40-65° C.) and collecting 100-cm³ fractions. Fractions34 to 82 were combined and then concentrated to dryness under the aboveconditions. 13.6 g of 1-(2-bromoethoxy)-2,3-difluorobenzene wereobtained in the form of a colorless fluid oil.

[3552]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 3.85 (broad t,J=6 Hz: 2H); 4.44 (broad t, J=6 Hz: 2H); 6.82 (mt: 1H); 7.18 (ddd, J=9-7and 3 Hz: 1H); 7.29 (ddd, J=11-9 and 5 Hz: 1H).

[3553] The benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride was prepared as described in Example 13.

EXAMPLE 184-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiazole-2-thioethyl)piperidine-4-carboxylicacid

[3554] A mixture of 0.3 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiazole-2-thioethyl)piperidine-4-carboxylatein 6 cm³ of aqueous 5N hydrochloric acid was maintained at a temperaturein the region of 100° C., with stirring and under an inert atmospherefor 6 hours. After cooling and stirring for 16 hours at a temperature inthe region of 20° C., the reaction mixture was concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.

[3555] The residue obtained was taken up in 10 cm³ of dichloroethanecontaining 10% methanol, and then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. The residueobtained was purified by chromatography under atmospheric pressure, on acolumn of silica gel (particle size 40-60μ; diameter 2.5 cm; height: 30cm), eluting with a dichloroethane/methanol/aqueous ammonia mixture(89/10/1 by volume). Fractions 18 to 41 were combined and thenconcentrated to dryness under the above conditions.

[3556] The residue obtained was taken up in 5 cm³ of isopropyl ether,filtered and dried in a desiccator under reduced pressure (0.1 kPa) at atemperature in the region of 40° C. 0.24 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiazole-2-thioethyl)piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 200° C.

[3557]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.34 (mt: 2H);1.55 (mt: 2H); 1.69 (mt: 2H); from 1.85 to 2.15 (mt: 4H); 2.59 (broad t,J=7 Hz: 2H); 2.67 (DMF, J=12 Hz: 2H); 3.17 (broad t, J=6 Hz: 2H); from3.20 to 3.50 (mt: 2H); 3.96 (s: 3H); 7.38 (broad s: 1H); 7.45 (broad dd,J=9 and 2.5 Hz: 1H); 7.63 (d, J=3 Hz: 1H); 7.71 (d, J=3 Hz: 1H); 7.96(d, J=9 Hz: 1H); 8.68 (s: 1H); from 11.90 to 12.55 (very broadunresolved peak: 1H).

Ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiazole-2-thioethyl)piperidine-4-carboxylate

[3558] 0.28 g of 2-mercaptothiazole, 0.33 g of potassium carbonate and0.39 g of potassium iodide were added to a solution of 0.9 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl) propyl]-1-(2-chloroethyl)piperidine-4-carboxylate in 50 cm³ of acetonitrile at a temperature inthe region of 20° C., with stirring and under an inert atmosphere. Afterheating for 20 hours at a temperature in the region of 80° C., thereaction mixture was cooled to about 20° C., filtered and concentratedto dryness under reduced pressure (2 kPa) at a temperature in the regionof 50° C.

[3559] The residue obtained was purified by chromatography under apressure of 100 kPa of nitrogen, on a column of silica gel (particlesize 40-60μ; diameter 3.5 cm; height 35 cm), eluting with adichloromethane/methanol mixture (95/0.5 by volume) and collecting40-cm³ fractions. The fractions containing the product were combined andthen purified by chromatography under a pressure of 100 kPa of nitrogen,on a column of silica gel (particle size 40-60μ; diameter 3.5 cm; height30 cm), eluting with an ethyl acetate/cyclohexane mixture (75/25 byvolume) and collecting 30-cm³ fractions. Fractions 23 to 40 werecombined and then concentrated to dryness as previously. 0.75 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiazole-2-thioethyl)piperidine-4-carboxylatewas obtained.

[3560]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.05 (t, J=7 Hz:3H); 1.38 (mt: 2H); 1.52 (mt: 2H); 1.68 (mt: 2H); from 1.90 to 2.05 (mt:4H); 2.59 (t, J=7 Hz: 2H); 2.68 (broad d, J=12 Hz: 2H); 3.17 (broad t,J=7.5 Hz: 2H); from 3.25 to 3.40 (mt: 2H); 3.97 (s: 3H); 4.00 (q, J=7Hz: 2H); 7.38 (d, J=2.5 Hz: 1H); 7.46 (dd, J=9 and 2.5 Hz: 1H); 7.63 (d,J=3.5 Hz: 1H); 7.71 (d, J 3.5 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.68 (s:1H).

Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-chloroethyl)piperidine-4-carboxylate

[3561] 1.21 cm³ of thionyl chloride were added to a solution of 1.8 g ofethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylatein 40 cm³ of dichloromethane with stirring, at a temperature in theregion of 20° C. After stirring for 48 hours at a temperature in theregion of 20° C., the reaction mixture was concentrated under reducedpressure (1 kPa) at a temperature in the region of 50° C.

[3562] The residue was taken up in 50 cm³ of water and 50 cm³ of ethylacetate with vigorous stirring at a temperature in the region of 20° C.,followed by addition of 10 g of potassium carbonate. The organic phasewas washed with 25 cm³ of water and then with 25 cm³ of saturated sodiumchloride solution, dried over magnesium sulfate, filtered andconcentrated under reduced pressure (1 kPa) at a temperature in theregion of 50° C. 1.8 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-chloroethyl)piperidine-4-carboxylatewere obtained.

[3563] Infra-red Spectrum (CCl₄): 2957; 1726; 1622; 1503; 1230; 1116;1029 and 833 cm−¹.

Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylate

[3564] 3.9 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylateand 2.07 g of potassium carbonate were added to a solution of 1.17 cm³of 2-iodoethanol in 80 cm³ of acetonitrile, at a temperature in theregion of 20° C. with stirring and under an inert atmosphere. Afterheating for 23 hours at a temperature in the region of 80° C., a further1.17 cm³ of 2-iodoethanol were added. After heating for 40 hours at atemperature in the region of 80° C., the reaction mixture was cooled toabout 20° C., filtered and concentrated under reduced pressure (1 kPa)at a temperature in the region of 50° C. The residue obtained waspurified by chromatography under a pressure of 100 kPa of nitrogen, on acolumn of silica gel (particle size 40-60μ; diameter 4 cm; height 60cm), eluting with a dichloromethane/methanol/aqueous ammonia mixture(89/10/1 by volume) and collecting 50-cm³ fractions. Fractions 14 to 17were combined and then concentrated as previously. 1.9 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylatewere obtained.

[3565] Infra-red Spectrum (CCl₄) : 2439; 2952; 1726; 1622; 1503; 1230;1116; 1029 and 833 cm⁻¹.

EXAMPLE 194-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-1-[2-(cyclopentylthioethyl)piperidin-4-yl]methanoldihydrochloride

[3566] A mixture of 0.6 g of{4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidin-4-yl}methanoldihydrochloride, 0.24 g of 1-bromo-2-(cyclopentylthio)ethyl, 0.22 g ofpotassium iodide and 0.9 g of potassium carbonate in 25 cm³ ofacetonitrile was heated with stirring for 20 hours at a temperature inthe region of 75° C. After cooling to a temperature in the region of 20°C., the reaction mixture was concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C.

[3567] The residue obtained was taken up in 20 cm³ of water and thenextracted with 3 times 20 cm³ of ethyl acetate. The organic phases werecombined, dried over magnesium sulfate, filtered and then concentratedto dryness as above. The residue obtained was purified by chromatographyunder a pressure of 50 kPa of nitrogen, on a column of silica gel(particle size 20-45μ; diameter 3 cm; height: 18 cm), eluting with adichloromethane/methanol mixture (90/10 by volume). The fractionscontaining the expected product were combined and then concentrated todryness under the above conditions. The residue obtained was taken up in5 cm³ of acetone and then acidified with 3 cm³ of a 1N solution ofhydrogen chloride in diethyl ether. The suspension obtained was dilutedwith 20 cm³ of diethyl ether, stirred at a temperature in the region of20° C. for 3 hours, filtered, washed with diethyl ether and then driedin a desiccator under reduced pressure (0.1 kPa) at a temperature in theregion of 40° C. 0.4 g of4-[3-(R,S)-hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthioethyl)piperidin-4-yl]methanoldihydrochloride was obtained in the form of a pale yellow solid meltingat 120° C.

[3568]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CD₃COOD-d₄ at a temperature of 373K, δ in ppm): from 1.20 to 2.15(mt: 16H); 2.93 (broad t, J=7.5 Hz: 2H); from 3.10 to 3.30 (mt: 7H);3.33 (broad s: 2H); 3.91 (s: 3H); 5.49 (mt: 1H); 7.41 (dd, J=9 and 3 Hz:1H); 7.93 (d, J=9 Hz: 1H); 8.22 (d, J=3 Hz: 1H); 8.60 (s: 1H).

{4-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidin-4-yl}methanol dihydrochloride

[3569] A mixture of 1.5 g of tert-butyl4-(tert-butyldimethylsilanyloxymethyl)-4-[3-(3-chloro-6-methoxy-quinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-1-carboxylatein 6.5 cm³ of 5N hydrochloric acid dissolved in dioxane and 30 cm³ ofdioxane was stirred at a temperature in the region of 20° C. for 17hours. 100 cm ³ of diethyl ether were added to the reaction mixture. Theprecipitate formed was filtered off to give 1.24 g of{4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidin-4-yl}methanoldihydrochloride in the form of a pale yellow solid.

[3570]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.20 to 2.10(mt: 8H); from 2.85 to 3.10 (mt: 4H); 3.26 (broad s: 2H); 3.91 (s: 3H);5.45 (mt: 1H); 7.47 (dd, J=9 and 3 Hz: 1H); 7.98 (d, J=9 Hz: 1H); 8.23(d, J=3 Hz: 1H); from 8.60 to 8.80 (unresolved peak: 2H); 8.69 (s: 1H).

tert-Butyl4-(tert-butyldimethylsilanyloxymethyl)-4-[3-(3-chloro-6-methoxy-quinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-1-carboxylate

[3571] A solution of 5.26 g of tert-butyl4-(tert-butyldimethylsilanyloxymethyl)-4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]piperidine-1-carboxylatein 300 cm³ of dimethyl sulfoxide and 75 cm³ of tert-butanol was stirredunder an oxygen-saturated atmosphere at a temperature in the region of20° C. After 5 minutes, a solution of 2.1 g of potassium tert-butoxidein 30 cm³ of tert-butanol was added to the reaction mixture. Aftersparging with oxygen for 1 and a half hours, the reaction mixture waspoured carefully onto a mixture of 300 g of ice, 300 cm³ of water and1.1 cm³ of acetic acid. The aqueous phase was extracted with 3 times 300cm³ of dichloromethane. The organic phases were combined, washed withtwice 300 cm³ of water, dried over magnesium sulfate and thenconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3572] The residue obtained was purified by chromatography under apressure of 50 kPa of nitrogen, on a column of silica gel (particle size20-45μ; diameter 4 cm; height: 27 cm), eluting with a cyclohexane/ethylacetate mixture (50/50 by volume). The fractions containing the expectedproduct were combined and then concentrated to dryness under the aboveconditions. 3.4 g of tert-butyl4-(tert-butyldimethylsilanyloxymethyl)-4-[3-(3-chloro-6-methoxy-quinolin-4-yl)-3-hydroxypropyl]piperidine-1-carboxylatewere obtained in the form of a white foam.

[3573] Mass spectrum: EI m/z=578 M^(+ m/z=)521C₂₆H₃₈ClN₂O₅Si^(+ m/z=)465 C₂₂H₃₀ClN₂O₅Si^(+ m/z=)421 C₂₁H₃₀ClN₂O₃Si⁺base peak m/z=57 C₄H₉ ^(+ DCI m/z=)579 MH^(+ m/z=)523 C₂₆H₄₀ClN₂O₅Si⁺

tert-Butyl4-(tert-butyldimethylsilanyloxymethyl)-4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]piperidine-1-carboxylate

[3574] A mixture of 0.45 g of tert-butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-hydroxymethyl-piperidine-1-carboxylate,0.3 g of tert-butyldimethylsilyl chloride, 0.17 cm³ of triethylamine and0.04 g of dimethylaminopyridine in 20 cm³ of dichloromethane was stirredunder an inert atmosphere at a temperature in the region of 20° C. Afterstirring for 18 hours, 0.3 g of tert-butyldimethylsilyl chloride, 0.04 gof dimethylaminopyridine and 0.2 cm³ of triethylamine were added. Thereaction mixture was taken up in 20 cm³ of water. The aqueous phase wasextracted with twice 20 cm³ of dichloromethane. The organic phases werecombined, washed with twice 300 cm³ of saturated sodium chloridesolution, dried over magnesium sulfate and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.

[3575] The residue obtained was purified by chromatography under apressure of 50 kPa of nitrogen, on a column of silica gel (particle size20-45μ; diameter 2.5 cm; height: 15 cm), eluting with acyclohexane/ethyl acetate mixture (70/30 by volume). The fractionscontaining the expected product were combined and then concentrated todryness under the above conditions. 0.48 g of tert-butyl4-(tert-butyldimethylsilanyloxymethyl)-4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]piperidine-1-carboxylatewas obtained in the form of a colorless lacquer.

[3576]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): −0.04 (s: 6H);0.76 (s: 9H); 1.29 (mt: 4H); 1.39 (s: 9H); 1.58 (mt: 4H); 3.19 (mt: 2H);from 3.20 to 3.45 (mt: 6H); 3.95 (s: 3H); 7.41 (d, J=3 Hz: 1H); 7.45(dd, J=9 and 3 Hz: 1H); 7.95 (d, J=9 Hz: 1H); 8.67 (s: 1H).

tert-Butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)]propyl]-4-hydroxymethylpiperidine-1-carboxylate

[3577] 1.05 g of lithium aluminum hydride was added portionwise, withstirring and under an inert atmosphere, to a solution of 12.3 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatein 250 cm³ of tetrahydrofuran, at a temperature in the region of −20° C.After stirring for 2 hours at a temperature in the region of 20° C., 0.5g of lithium aluminum hydride was added to the reaction mixture at atemperature in the region of −20° C. After 1 and a half hours, thereaction mixture was cooled to 0° C. and was then hydrolyzed bysuccessive addition of 1.8 cm³ of water, 1.3 cm³ of 5N sodium hydroxideand 5.7 cm³ of water. After stirring for 30 minutes at a temperature inthe region of 20° C., the reaction mixture was filtered and then washedwith 400 cm³ of ethyl acetate. The filtrate was washed with 200 cm³ ofsaturated sodium chloride solution, dried over magnesium sulfate andthen concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. 10.9 g of tert-butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-hydroxymethylpiperidine-1-carboxylatewere obtained.

[3578]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.23 (mt: 2H);1.32 (mt: 2H); 1.39 (s: 9H); 1.58 (mt: 4H); from 3.10 to 3.40 (mt: 6H);3.22 (d, J=5 Hz: 2H); 3.96 (s: 3H); 4.50 (t, J=5 Hz: 1H); 7.40 (d, J=3Hz: 1H); 7.45 (dd, J=9 and 3 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.68 (s:1H).

[3579] The ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatewas prepared as described in Example 5.

EXAMPLE 204-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-(3-phenylpropyl)piperidin-4-carboxylicacid

[3580] A mixture of 0.5 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-(3-phenyl-propyl)piperidine-4-carboxylatein 8 cm³ of aqueous 5N hydrochloric acid was maintained at a temperaturein the region of 100° C., with stirring for 6 hours. After stirring for18 hours at a temperature in the region of 20° C., the reaction mixturewas concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. The residue obtained was taken up in10 cm³ of dichloromethane and filtered. The filtrate was concentrated todryness as above, taken up in diisopropyl ether and then dried in adesiccator under reduced pressure (0.1 kPa) at a temperature in theregion of 40° C.

[3581] The residue obtained was purified by chromatography under apressure of 60 kPa of nitrogen, on a column of silica gel (particle size20-45μ; diameter 2.5 cm; height: 40 cm); eluting with a mixture ofdichloromethane/methanol/aqueous ammonia (83/15/2). Fractions 13 to 20were combined and then concentrated to dryness under the aboveconditions. 0.24 g of4-[3-(3-chloro-6-methoxy-quinolin-4-yl)-3-(R,S)-fluoropropyl]-1-(3-phenylpropyl)piperidin-4-carboxylicacid was obtained in the form of a white solid melting at 240° C.

[3582]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) from 1.20 to 2.35and from 2.40 to 2.70 (mts: 18H in total); 3.94 (broad s: 3H); 6.36 (2mts, J_(HF)=48 Hz: 1H); from 7.10 to 7.35 (mt: 5H); 7.52 (broad d, J=9Hz: 1H); 7.57 (broad s: 1H); 8.02 (broad d, J=9 Hz: 1H); 8.75 (broad s:1H).

Methyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-(3-phenylpropyl)piperidine-4-carboxylate

[3583] 0.31 cm³ of diethylaminosulfur trifluoride was added to asolution of 0.66 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-(3-phenyl-propyl)piperidine-4-carboxylatein 40 cm³ of dichloromethane, with stirring and under an inertatmosphere, at a temperature in the region of −15° C. After stirring for3 hours at a temperature in the region of 20° C., 0.31 cm³ ofdiethylaminosulfur trifluoride was added to the reaction mixture,followed by 20 cm³ of saturated sodium hydrogen carbonate solution. Theaqueous phase was extracted with 20 cm³ of dichloromethane. The organicphases were combined, washed with saturated sodium chloride solution,dried over magnesium sulfate and then concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C.

[3584] The residue obtained was purified by chromatography under apressure of 100 kPa of nitrogen, on a column of silica gel (particlesize 20-45μ; diameter 3.5 cm; height: 35 cm), eluting with adichloromethane/methanol mixture (97/3). Fractions 15 to 21 werecombined and then concentrated to dryness according to the aboveconditions. 0.5 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-(3-phenylpropyl)piperidine-4-carboxylatewas obtained in the form of a brown oil.

[3585]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) from 1.30 to 2.35and from 2.50 to 2.80 (mts: 18H in total); 3.54 (s: 3H); 3.93 (s: 3H);6.36 (ddd, J_(HF)=48-8.5 and 4.5 Hz: 1H); 7.19 (mt: 3H); 7.29 (broad t,J=7.5 Hz: 2H); 7.52 (mt: 2H); 8.04 (d, J=9 Hz: 1H); 8.75 (broad s: 1H).

Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-(3-phenylpropyl)piperidine-4-carboxylate

[3586] A mixture of 1 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-4-carboxylate,0.58 g of 1-bromo-3-phenylpropane and 0.53 g of potassium carbonate in50 cm³ of acetonitrile was heated for 22 hours at a temperature in theregion of 75° C., with stirring and under an inert atmosphere. Aftercooling to a temperature in the region of 20° C., the reaction mixturewas filtered and washed with acetonitrile. The filtrate was concentratedto dryness under reduced pressure (2 kPa) at a temperature in the regionof 40° C.

[3587] The residue obtained was purified by chromatography under apressure of 100 kPa of nitrogen, on a column of silica gel (particlesize 70-200μ; diameter 3.5 cm; height: 40 cm), eluting withdichloromethane/methanol (95/05). Fractions 21 to 48 were combined andthen concentrated to dryness under the above conditions. 0.7 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-(3-phenylpropyl)piperidine-4-carboxylatewas obtained.

[3588]¹H NMR Spectrum (300 MHz, (CD₃)2SO-d₆, δ in ppm) from 1.20 to 2.35and from 2.45 to 2.75 (mts: 18H in total); 3.48 (s: 3H); 3.88 (s: 3H);5.40 (mt: 1H); 6.07 (d, J=4 Hz: 1H); from 7.20 to 7.25 (mt: 3H); 7.27(broad t, J=7.5 Hz: 2H); 7.44 (dd, J=9 and 3 Hz: 1H); 9.96 (d, J=9 Hz:1H); 8.14 (d, J=3 Hz: 1H); 8.66 (s: 1H).

[3589] The methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-4-carboxylatewas prepared as described in Example 49.

EXAMPLE 21

[3590] Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidine-4-carboxylatewas prepared in the form of a yellow oil.

[3591]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.35 to1.60 (mt: 4H); 1.74 (mt: 2H); from 1.95 to 2.10 (mt: 4H); 2.40 (t, J=7Hz: 2H); from 2.60 to 2.75 (mt: 2H); 3.07 (mt: 2H); 3.15 (broad t, J=7.5Hz: 2H); 3.94 (s: 3H); 5.05 (s: 2H); 6.05 (broad t, J 5 Hz: 1H); from6.15 to 6.30 (mt: 3H); 7.27 (mt: 5H); 7.36 (d, J=2.5 Hz: 1H); 7.47 (dd,J=9 and 2.5 Hz: 1H); 7.98 (d, J=9 Hz: 1H); 8.68 (s: 1H).

4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidin-4-carboxylicacid

[3592] A mixture of 0.73 g of benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluoro-phenylamino)ethyl]piperidine-4-carboxylatein 12 cm³ of aqueous 5N hydrochloric acid was maintained at atemperature in the region of 100° C. with stirring for 3.5 hours. Aftercooling to about 20° C., the reaction mixture was evaporated underreduced pressure (2 kPa) at a temperature in the region of 50° C. Theevaporation residue obtained was taken up in 50 cm³ of acetone and wasthen concentrated to dryness under the same conditions as above.

[3593] The foam obtained was purified by chromatography under a pressureof 50 kPa of argon, on a column of silica gel (particle size 20-45μ;diameter 2.5 cm; height 38 cm), eluting with a mixture ofchloroform/methanol/aqueous ammonia (12/3/0.5 by volume). Fractions 31to 46 were combined and then concentrated to dryness under the sameconditions as above. The powder obtained was dried in an oven underreduced pressure (0.1 kPa) at a temperature in the region of 40° C. 0.28g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenylamino)ethyl]piperidin-4-carboxylicacid was obtained in the form of a pink-white solid melting at 210° C.

[3594]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.45 (broad t,J=12.5 Hz: 2H); 1.56 (mt: 2H); 1.68 (mt: 2H); from 1.90 to 2.10 (mt:4H); 2.41 (t, J=6.5 Hz: 2H); 2.66 (broad d, J=12 Hz: 2H); 3.08 (mt: 2H);3.18 (broad t, J=7.5 Hz: 2H); 3.97 (s: 3H); 6.08 (broad t, J=4.5 Hz:1H); from 6.15 to 6.30 (mt: 3H); 7.38 (d, J=2.5 Hz: 1H); 7.45 (dd, J=9and 2.5 Hz: 1H); 7.96 (d, J=9 Hz: 1H: 1H); 8.68 (s: 1H).

EXAMPLE 224-[3-(R,S)-Hydroxy-3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-1-[2-(thien-3-yl)thioethyl]piperidin-4-ylmethanol

[3595] A mixture of 0.6 g of{4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidin-4-yl)methanol dihydrochloride, 0.34 g of 2-(2-bromo-ethylthio)thiophene, 0.95g of potassium carbonate and 0.23 g of potassium iodide in 25 cm³ ofacetonitrile was heated for 17 hours at a temperature in the region of80° C., with stirring and under an inert atmosphere. After cooling to atemperature in the region of 20° C., the reaction mixture was dilutedwith 30 cm³ of water and was then extracted with twice 30 cm³ of ethylacetate. The organic extracts were combined, dried over magnesiumsulfate, filtered and then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C.

[3596] The oil obtained was purified by chromatography under a pressureof 50 kPa of argon, on a column of silica gel (particle size 20-45μ;diameter 3 cm; height 27 cm), eluting with a mixture ofdichloromethane/methanol (93/7 by volume). The fractions containing theproduct were combined and then concentrated to dryness under the aboveconditions. The oil obtained was acidified with 2 cm³ of 1N hydrochloricether, diluted with 20 cm³ of diethyl ether and stirred for 1 hour at atemperature in the region of 20° C. The solid was filtered off, washedwith diethyl ether and then dried in an oven under reduced pressure (10kPa) at a temperature in the region of 40° C. 0.28 g of4-[3-(R,S)-hydroxy-3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-1-[2-thien-3-yl)thioethyl]piperidin-4-yl}methanol hydrochloride was obtained in the form of a yellow solidmelting at 118° C. and becoming pasty.

[3597]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆, δ in ppm) A mixture of twodiastereoisomers in 50/50 approximate proportions was observed.

[3598] * from 1.35 to 2.10 (mt: 8H); from 2.85 to 3.60 (mt: 10H); 3.86and 3.87 (2s: 3H in total); 5.41 (mt: 1H); from 5.80 to 6.30 (broadunresolved peak: 1H); 7.10 (mt: 1H); 7.29 (mt: 1H); 7.43 (dd, J=9 and 3Hz: 1H); 7.70 (mt: 1H); 7.94 (d, J=9 Hz: 1H); 8.19 (broad s: 1H); 8.64(s: 1H); 9.48 (unresolved peak: 1H).

[3599]{4-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidin-4-yl}methanol dihydrochloride was prepared as described in Example 19.

EXAMPLE 234-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxamide

[3600] 15.6 cm³ of a 0.5N solution of aqueous ammonia in dioxane, 0.26 gof 1-hydroxybenzotriazole hydrate, 0.75 g of1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride and 0.55cm³ of triethylamine were added to a mixture of 0.75 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylicacid in the form of the sodium salt, in 20 cm³ of dichloromethane. Thesuspension obtained was stirred for 17 hours at a temperature in theregion of 20° C. The reaction mixture was diluted with 25 cm³ of waterand stirred, and the phases were then separated by settling. The aqueousphase was extracted with twice 25 cm³ of dichloromethane and the organicextracts were combined, washed with 25 cm³ of brine, dried overmagnesium sulfate and then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. Theevaporation residue obtained was purified by chromatography under apressure of 50 kPa of argon, on a column of silica gel (particle size20-45μ; diameter 3 cm; height 21 cm), eluting with a mixture ofdichloromethane/methanol (90/10 by volume). The fractions containing theproduct were combined and then concentrated to dryness under the aboveconditions. 0.22 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxamidewas obtained in the form of a white solid melting at 160° C.

[3601]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.33 (broad t,J=12 Hz: 2H); 1.53 (mt: 2H); 1.67 (mt: 4H); 1.98 (mt: 4H); 2.20 (t,J=7.5 Hz: 2H); from 2.40 to 2.60 (mt: 4H); 3.15 (t, J=7.5 Hz: 2H); 3.97(s: 3H); 6.87 (s: 1H); 7.10 (s: 1H); 7.17 (mt: 1H); 7.20 (broad d, J=7.5Hz: 2H); 7.27 (broad t, J=7.5 Hz: 2H); 7.37 (d, J=2.5 Hz: 1H); 7.45 (dd,J=9 and 2.5 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.68 (s: 1H).

[3602] The4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-(3-phenylpropyl)piperidine-4-carboxylicacid dihydrochloride was prepared as described in Example 4.

EXAMPLE 244-[3-(3-Chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylicacid

[3603] 26 cm³ of aqueous 5N sodium hydroxide and 20 cm³ of methanol wereadded to a solution of 1.47 g of ethyl4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylatein 20 cm³ of dioxane, with stirring and at a temperature in the regionof 20° C., and the mixture was then maintained at a temperature of about70° C. for 21 hours. The reaction mixture was concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.The residue obtained was purified by chromatography under a pressure of50 kPa of argon, on a column of silica gel (particle size 40-63μ; mass60 g), eluting with a mixture of dichloromethane/methanol/aqueousammonia (12/3/0.5 by volume). Fractions 11 to 25 were combined and thenconcentrated to dryness under the above conditions. 1.03 g of4-[3-(3-chloro-6,7-dimethoxy-quinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]-piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 214° C.

[3604]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.27 (very broadt, J=12 Hz: 2H); from 1.45 to 1.75 (mt: 4H); from 1.85 to 2.10 (mt: 4H);2.44 (mt: 2H); from 2.50 to 2.65 (mt: 2H); 2.89 (broad t, J=7.5 Hz: 2H);3.13 (mt: 2H); 3.93 (s: 3H); 3.96 (s: 3H); 7.02 (dd, J=5.5 and 3.5 Hz:1H); 7.15 (dd, J=3.5 and 1 Hz: 1H); 7.30 (broad s: 1 H); 7.38 (broad s:1H); 7.58 (dd, J=5.5 and 1 Hz: 1H); 8.58 (s: 1H).

Ethyl4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-[2-(thiophene-2-ylthio)ethyl]piperidine-4-carboxylate

[3605] A mixture of 1.65 g of ethyl4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)piperidine-4-carboxylate, 1.16g of 2-(2-bromoethylthio)thiophene, 1.63 g of potassium carbonate and0.685 g of potassium iodide in 50 cm³ of acetonitrile was stirred for 23hours at a temperature in the region of 20° C. The suspension wasfiltered and the filtrate was then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C.

[3606] The evaporation residue was taken up in 50 cm³ of ethyl acetate,washed with twice 50 cm³ of water and with 40 cm³ of saturated aqueoussodium chloride solution, dried over magnesium sulfate, filtered andconcentrated to dryness under the above conditions. The oil obtained waspurified by chromatography under a pressure of 50 kPa of argon, on acolumn of silica gel (particle size 40-63μ; diameter 4 cm), eluting witha mixture of dichloromethane/methanol/acetonitrile (95/2.5/2.5 byvolume). The fractions containing the product were combined and thenconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. 1.47 g of4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylicacid were obtained in the form of an oil.

[3607]¹H NMR spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.05 (t, J=7 Hz:3H); 1.37 (broad t, J=12 Hz: 2H); 1.52 (mt: 2H); from 1.60 to 1.75 (mt:2H); from 1.85 to 2.05 (mt: 4H); 2.46 (mt: 2H); 2.61 (broad d, J=12 Hz:2H); 2.91 (mt: 2H); 3.15 (broad t, J=7.5 Hz: 2H); 3.95 (s: 3H); 3.97 (s:3H); 4.00 (q, J=7 Hz: 2H); 7.04 (dd, J=5.5 and 3.5 Hz: 1H); 7.17 (dd,J=3.5 and 1 Hz: 1H); 7.31 (broad s: 1H); 7.40 (broad s: 1H); 7.60 (dd,J=5.5 and 1 Hz: 1H); 8.61 (s: 1H).

Ethyl 4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)piperidine-4-carboxylate

[3608] 3 cm³ of trifluoroacetic acid were added dropwise to a mixture of2.05 g of ethyl4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatein 20 cm³ of dichloromethane, with stirring and at a temperature in theregion of 20° C. After 2 hours, the reaction mixture was concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of40° C. The residue was taken up in 20 cm³ of water and 10 cm³ of ethylacetate, and then extracted with twice 10 cm³ of aqueous 1N hydrochloricacid solution. The aqueous phase was basified with an aqueous 30% sodiumhydroxide solution until the pH was about 10, and then extracted with 3times 30 cm³ of ethyl acetate. The organic extracts were combined, driedover magnesium sulfate, filtered and then concentrated to dryness asabove. 1.65 g of ethyl4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)piperidine-4-carboxylate wereobtained in the form of a yellow oil.

[3609] Mass Spectrum: EI m/z=420 M⁺ m/z=364 C₁₉H₂₃ClNO₄ ^(+ m/z=)264C₁₄H₁₅ClNO₂ ⁺ m/z=237 C₁₂H₁₂ClNO₂ ⁺ base peak m/z=184 C₁₀H₁₈NO₂ ⁺

Ethyl 4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

[3610] 21 cm³ of 0.5M 9-borabicyclo[3.3.1]nonane solution were cooled toa temperature in the region of 0° C. and 2.61 g of ethyl4-allyl-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate in 26 cm³ oftetrahydrofuran were added dropwise, with stirring and under an inertatmosphere, while maintaining the temperature at about 0° C. After theaddition, the temperature of the mixture was returned to about 20° C.The solution obtained was stirred for a further 4 hours at thistemperature, followed by addition of 37 cm³ of dioxane, 0.19 g ofpalladiumdiphenylphosphinoferrocene chloride, 3.05 g of4-bromo-3-fluoro-6-methoxyquinoline and 5.58 g of tribasic potassiumphosphate. After stirring for 24.75 hours at a temperature in the regionof 60° C., the reaction mixture was cooled to about 20° C. and filtered,and the filtrate was then concentrated to dryness under reduced pressure(2 kPa) at a temperature in the region of 40° C.

[3611] The residue obtained was taken up in 100 cm³ of ethyl acetate and100 cm³ of water, the phases were separated by settling and the organicphase was then washed with 100 cm³ of saturated sodium chloridesolution. The organic phase was dried over magnesium sulfate, filteredand concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. The oil obtained was purified bychromatography, under a pressure of 50 kPa of argon, on a column ofsilica gel (particle size 40-63μ; volume 690 cm³), eluting with adichloromethane/methanol/ acetonitrile mixture (98/1/1 by volume). Thefractions containing the product were combined and then concentrated todryness according to the same conditions as above. 2.16 g of ethyl4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatewere obtained in the form of a yellow gel.

[3612]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.06 (t, J=7 Hz:3H); from 1.25 to 1.45 (mt: 2H); 1.39 (s: 9H); 1.53 (mt: 2H); 1.69 (mt:2H); 1.93 (broad d, J=13.5 Hz: 2H), 2.82 (unresolved peak: 2H); 3.14(broad t, J=7.5 Hz: 2H); 3.69 (broad d, J=13.5 Hz: 2H); 3.94 (s: 3H);3.97 (s: 3H); 4.03 (q, J=7 Hz: 2H); 7.31 (broad s: 1H); 7.40 (broad s:1H); 8.61 (s: 1H).

4-Bromo-3-chloro-6,7-dimethoxyquinoline

[3613] 19 g of triphenylphosphine dibromide were added to a solution of5.39 g of 3-chloro-4-hydroxy-6,7-dimethoxyquinoline in 270 cm³ ofacetonitrile, with stirring and at a temperature in the region of 20° C.The reaction mixture was heated at about 80° C. for 8.25 hours. Aftercooling to a temperature in the region of 20° C., the insoluble materialwas filtered off. 5.67 g of 4-bromo-3-chloro-6,7-dimethoxyquinoline wereobtained in the form of a gray solid.

[3614] Mass spectrum: DCI m/z=302 MH⁺

3-Chloro-4-hydroxy-6,7-dimethoxyquinoline

[3615] 5.45 g of N-chlorosuccinimide were added to a solution of6,7-dimethoxyquinolin-4-ol in 300 cm ³ of acetic acid, with stirring andat a temperature in the region of 20° C. The reaction mixture was heatedat a temperature in the region of 50° C. for 6 hours. After cooling toabout 20° C. and stirring for 18 hours at this same temperature, thereaction mixture was concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. One hundred cm³ of sodiumhydrogen carbonate solution were added dropwise to the evaporationresidue and the suspension was then stirred for 24 hours in the regionof 20° C. The insoluble material was filtered off and then dried in anoven under reduced pressure (20 Pa). 5.39 g of3-chloro-4-hydroxy-6,7-dimethoxyquinoline were obtained in the form of adark green solid.

[3616] Mass spectrum: DCI m/z=240 MH⁺

6,7-Dimethoxy-4-hydroxyquinoline

[3617] A mixture of 9.24 g of4-hydroxy-6,7-dimethoxyquinoline-3-carboxylic acid in 185 cm³ ofdiphenyl ether was maintained, with mechanical stirring, at atemperature in the region of 250° C. for 1.3 hours. After cooling thereaction mixture to about 20° C., 100 cm³ of diisopropyl ether wereadded. The suspension was stirred for 8 hours and filtered, and thefilter cake was washed with 3 times 100 cm³ of diisopropyl ether. 7.96 gof 6,7-dimethoxyquinolin-4-ol were obtained in the form of a brownsolid.

[3618] Infra-red spectrum (KBr): 3242; 1605; 1548; 1500; 1273; 1239;1220; 1075 and 822 cm⁻¹.

4-Hydroxy-6,7-dimethoxyquinoline-3-carboxylic acid

[3619] 10.2 g of phosphorus pentoxide were added cautiously, withmechanical stirring, to a mixture of 21.1 g of diethyl2-[(3,4-dimethoxyphenylamino)methylene]malonate in 42 cm³ ofnitrobenzene. The reaction mixture was maintained at a temperature inthe region of 150° C. for 4 hours. After cooling to about 20° C. andstirring for 18 hours at this same temperature, 14 cm³ of water wereadded dropwise and the reaction mixture was then heated to about 110° C.for 7 hours. After cooling to a temperature in the region of 20° C., 42cm³ of ethyl acetate were added. The suspension was stirred under theseconditions for 18 hours, the phases were then separated by settling, theorganic phase was filtered and the filter cake was washed with 3 times40 cm³ of ethyl acetate, 40 cm³ of ethanol and 40 cm³ of water. 9.25 gof 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylic acid were obtained inthe form of a cream-colored solid.

[3620] Infra-red spectrum (KBr): 2842; 1673; 1631; 1590; 1503; 1437;1279; 1220; 1006; 807; 586 and 357 cm⁻¹.

Diethyl 2-[(3,4-dimethoxyphenylamino)methylene]malonate

[3621] A mixture of 10 g of 3,4-dimethoxyaniline in 13.2 cm³ of diethylethoxymethylenemalonate was stirred for 1.5 hours at a temperature inthe region of 110° C. After cooling to about 20° C., the reactionmixture was concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 50° C. 21.1 g of diethyl2-[(3,4-dimethoxyphenylamino)methylene]malonate were obtained in theform of a brown solid.

[3622] Mass spectrum: DCI m/z=324 MH⁺

[3623] The ethyl4-allyl-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate was preparedas described in Example 1.

EXAMPLE 254-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylic acid monohydrochloride

[3624] 5 cm³ of aqueous 5N sodium hydroxide were added to a solution of0.6 g of(R,S)-3-(3-chloro-6-methoxyquinolin-4-yl)-9-[2-(2,5-difluorophenylthio)ethyl]-2-oxa-9-azaspiro[5.5]undecan-1-onein 50 cm³ of acetone, with stirring and at a temperature in the regionof 20° C. After 2 hours, the reaction mixture was concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of40° C. The evaporation residue was slurried in 10 cm³ of diethyl etherand filtered, and the filter cake was washed with diethyl ether and thendried in an oven under reduced pressure (10 Pa) at a temperature in theregion of 50° C.

[3625] The solid was taken up in water and acidified with aqueous 1Nhydrochloric acid solution until the pH was equal to 3. Dichloromethanewas added at a temperature in the region of 20° C. with moderatestirring and the solid was then filtered off. 0.32 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylicacid monohydrochloride was obtained in the form of a white solid.

[3626]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm) from 1.30 to 2.35(mt: 8H); 2.84 (unresolved peak: 2H); from 3.05 to 3.70 (mt: 6H); 3.90(broad s: 3H); 5.43 (unresolved peak: 1H); 6.16 (unresolved peak: 1H);7.14 (unresolved peak: 1H); 7.33 (unresolved peak: 1H); 7.46 (mt: 2H);7.96 (broad d, J=9 Hz: 1H); 8.16 (broad s: 1H); 8.67 (broad s: 1H); from10.20 to 10.60 (broad unresolved peak: 1H).

3-(3-Chloro-6-methoxyquinolin-4-yl)-9-[2-(2,5-difluorophenylthio)ethyl]-2-oxa-9-azaspiro[5.5]undecan-1-one

[3627] A mixture of 1.75 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-(R,S)-propyl]piperidine-4-carboxylatedihydrochloride, 0.95 g of 2-(2-bromoethylthio)-1,4-difluorobenzene,0.62 g of potassium iodide and 3.11 g of potassium carbonate in 30 cm³of acetonitrile and 20 cm³ of dimethylformamide was heated with stirringfor 18 hours at a temperature in the region of 85° C. After cooling toabout 20° C., the reaction mixture was filtered through Celite and thefiltrate was then concentrated to dryness under reduced pressure (2 kPa)at a temperature in the region of 40° C.

[3628] The residue obtained was taken up in water and diethyl ether. Theorganic phase was dried over magnesium sulfate, filtered and thenconcentrated to dryness as above. The residue obtained was purified bychromatography under atmospheric pressure, on a column of silica gel(particle size 70-200μ; diameter 4 cm), eluting with adichloromethane/methanol mixture (97.5/2.5 by volume). The fractionscontaining the product were combined and then concentrated to drynessunder the above conditions. 0.6 g of3-(3-chloro-6-methoxyquinolin-4-yl)-9-[2-(2,5-difluorophenylthio)ethyl]-2-oxa-9-azaspiro[5.5]undecan-1-onewas obtained.

[3629] Mass spectrum: EI m/z=532 M⁺ m/z=373 C₂₀H₂₂ClN₂O₃ ⁺ base peak

[3630] The 2-(2-bromoethylthio)-1,4-difluorobenzene was prepared asdescribed in Example 14.

[3631] The methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-4-carboxylatewas prepared as described in Example 49.

EXAMPLE 264-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylate

[3632] A mixture of 0.4 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylatein 6.6 cm³ of aqueous 5N hydrochloric acid was maintained at atemperature in the region of 100° C. with stirring for 6 hours. Aftercooling to about 20° C., the reaction mixture was stirred for 20 hoursat this same temperature and then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. The residuewas taken up in a dichloromethane/methanol mixture (90/10 by volume) andwas then concentrated to dryness again under the above conditions.

[3633] The evaporation residue was purified by chromatography under apressure of 60 kPa of argon, on a column of silica gel (particle size40-60μ; diameter 2.5 cm; height 41 cm), eluting with adichloromethane/methanol/28% aqueous ammonia mixture (83/15/2 by volume)and collecting 30-cm³ fractions. Fractions 16 to 22 were combined andthen concentrated to dryness under the above conditions. The residue wasslurried in 10 cm³ of diisopropyl ether, filtered and dried. 0.21 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-carboxylicacid was obtained in the form of an off-white solid melting at 205° C.

[3634]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.20 to1.70 (mt: 3H); from 1.80 to 2.40 (mt: 7H); from 2.30 to 2.80 (mt: 2H);2.61 (t, J=6 Hz: 2H); 3.92 (s: 3H); 4.17 (t, J=6 Hz: 2H); 6.36 (d mt,J_(HF)=48 Hz: 1H); from 6.65 to 6.85 (mt: 3H); 7.51 (dd, J=9 and 2.5 Hz:1H); 7.55 (broad s: 1H); 8.02 (d, J=9 Hz: 1H); 8.74 (s: 1H).

Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-carboxylate

[3635] 0.4 cm³ of diethylaminosulfur trifluoride was added to a solutionof 1.1 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylatein 50 cm³ of dichloromethane, with stirring and under an inertatmosphere, at a temperature in the region of −10° C. After stirring for4 hours at a temperature in the region of 20° C., 0.4 cm³ ofdiethylaminosulfur trifluoride was added to the reaction mixture and themixture was then stirred for 20 hours at this same temperature. 20 cm³of saturated aqueous sodium hydrogen carbonate solution were added. Theaqueous phase was extracted with 25 cm³ of dichloromethane. The organicphase was washed with twice 25 cm³ of aqueous 10% (by weight) sodiumchloride solution, dried over magnesium sulfate and then concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of40° C.

[3636] The oil obtained was purified by chromatography under a pressureof 100 kPa of argon, on a column of silica gel (particle size 40-60μ;diameter 3.5 cm; height: 35 cm), eluting with a dichloromethane/methanolmixture (97/3) and collecting 35-cm³ fractions. Fractions 20 to 21 werecombined and then concentrated to dryness under the above conditions.0.62 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-carboxylatewas obtained in the form of an orange-colored oil.

[3637] Infra-red spectrum: (CH₂Cl₂): 2953; 1725; 1622; 1599; 1504; 1466;1234; 1152; 1117 and 837 cm⁻¹.

Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-carboxylate

[3638] 0.47 cm³ of thionyl chloride was added dropwise, with stirringand under an inert atmosphere, to a mixture of 1.1 g of3-(3-chloro-6-methoxyquinolin-4-yl)-9-[2-(3,5-difluorophenoxy)ethyl]-2-oxa-9-azaspiro[5.5]undecan-1-onein 20 cm³ of methanol cooled to −20° C., and the mixture was thenstirred for 24 hours at a temperature in the region of 20° C. Thereaction mixture was concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. The residue was taken upin 30 cm³ of ethyl acetate and 15 cm³ of water. After addition of 5 g ofpotassium carbonate and vigorous stirring for 5 minutes, the mixture wasallowed to settle and the organic phase was separated out and washedwith 3 times 15 cm³ of aqueous 10% (by weight) sodium chloride solution.After drying over magnesium sulfate and then filtration, the organicsolution was concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. 1.12 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(3,5-difluorophenoxy)ethyl]-piperidine-4-carboxylatewere obtained in the form of a brown lacquer.

[3639] Infra-red spectrum (CCl₄): 3615; 2952; 1732; 1622; 1600; 1466;1233; 1154; 1117; 841 and 671 cm⁻¹.

3-(3-Chloro-6-methoxyquinolin-4-yl)-9-[2-(3,5-difluorophenoxy)ethyl]-2-oxa-9-azaspiro[5.5]undecan-1-one

[3640] A mixture of 1 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-4-carboxylate,0.8 g of 1-(2-bromoethoxy)-3,5-difluorobenzene and 0.42 g of potassiumcarbonate in 45 cm³ of acetonitrile was maintained at a temperature of80° C. with stirring and under an argon atmosphere for 20 hours. Thesuspension was filtered, the insoluble material was washed with ethylacetate and the filtrate was then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. The residuewas purified by chromatography under a pressure of 100 kPa of argon, ona column of silica gel (particle size 40-60μ; diameter 3.5 cm; height:38 cm), eluting with a dichloromethane/methanol mixture (97/4 by volume)and collecting 35-cm³ fractions. Fractions 9 to 20 were combined andthen concentrated to dryness under the above conditions. 1.1 g of3-(3-chloro-6-methoxyquinolin-4-yl)-9-[2-(3,5-difluorophenoxy)ethyl]-2-oxa-9-azaspiro[5.5]undecan-1-onewere obtained.

[3641] Infra-red spectrum (CCl₄): 2940; 1735; 1622; 1600; 1503; 1467;1233; 1153; 1117; 841 and 671 cm⁻¹.

[3642] The methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-hydroxypropyl]piperidine-4-carboxylatewas prepared as described in Example 49.

[3643] The 1-(2-bromoethoxy)-3,5-difluorobenzene may be obtained byapplying the method described in Example 16.

EXAMPLE 274-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxamide

[3644] 13.4 cm³ of a 0.5N solution of aqueous ammonia in dioxane, 0.229g of 1-hydroxybenzotriazole hydrate, 0.64 g of1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride and 0.46cm³ of triethylamine were added, with stirring and under an inertatmosphere, to a mixture of 0.69 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid in 30 cm³ of dichloromethane. The suspension obtained was stirredfor 17 hours at a temperature in the region of 20° C. The reactionmixture was diluted with 50 cm³ of water, stirred and the phases wereseparated by settling. The aqueous phase was extracted with twice 25 cm³of dichloromethane and the organic extracts were combined, washed with25 cm³ of saturated aqueous sodium chloride solution, dried overmagnesium sulfate and then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. The solid wastaken up in 20 cm³ of diisopropyl ether, stirred and then filtered. 0.52g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxamidewas obtained.

[3645]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.34 (broad t,J=12.5 Hz: 2H); 1.54 (mt: 2H); 1.66 (mt: 2H); 2.02 (broad d, J=12.5 Hz:2H); 2.12 (broad t, J=11 Hz: 2H); from 2.55 to 2.75 (mt: 4H); 3.16(broad t, J=7.5 Hz: 2H); 3.97 (s: 3H); 4.08 (t, J=6Hz: 2H); from 6.65 to6.85 (mt: 3H); 6.91 (broad s: 1H); 7.15 (broad s: 1H); 7.37 (d, J=3 Hz:1H); 7.45 (dd, J=9 and 3 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.68 (s: 1H).

[3646] The4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid was prepared as described in Example 2.

EXAMPLE 28 Sodium salt of4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-1-(cinnamyl)piperidine-4-carboxylicacid

[3647] A mixture of 0.72 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(cinnamyl)piperidine-4-carboxylatein 14 cm³ dioxane, 14 cm³ of methanol and 14 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 20° C.After 2 hours, a further 14 cm³ of aqueous 5N sodium hydroxide solutionwere added, followed by a further 14 cm³ after a further 18 hours. Thereaction mixture was maintained at a temperature in the region of 70° C.for 21 hours. After cooling to about 20° C., the reaction mass wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was taken up in 15 cm³ ofdistilled water, filtered and then dried in the open air for 18 hours.0.49 g of the sodium salt of sodium salt of4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-1-(cinnamyl)piperidine-4-carboxylicacid was obtained in the form of a white solid melting at about 230° C.

[3648]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.16 (very broadt, J=12 Hz: 2H); from 1.45 to 1.70 (mt: 4H); from 1.95 to 2.20 (mt: 4H);from 2.45 to 2.60 (mt: 2H); 2.99 (d, J=6.5 Hz: 2H); 3.14 (broad t, J=7Hz: 2H); 3.99 (s: 3H); 6.28 (dt, J=15.5 and 6.5 Hz: 1H); 6.48 (d, J=15.5Hz: 1H); 7.24 (broad t, J=7.5 Hz: 1H); 7.33 (broad t, J=7.5 Hz: 2H);from 7.40 to 7.50 (mt: 4H); 7.95 (d, J=9 Hz: 1H) ; 8.66 (s: 1H).

Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(cinnamyl)piperidine-4-carboxylate

[3649] A mixture of 1 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.551 g of cinnamyl bromide, 0.42 g of potassium iodide and 1.05 g ofpotassium carbonate in 20 cm³ of acetonitrile was stirred for 18.5 hoursat a temperature in the region of 20° C. The reaction mixture wasfiltered and the insoluble material was rinsed with 20 cm³ ofacetonitrile and with twice 30 cm³ of dichloromethane. The filtrate wasdried over magnesium sulfate, filtered and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.

[3650] The residue obtained was purified by chromatography under apressure of 50 kPa of argon, on a column of silica gel (particle size40-63μ; diameter 2.5 cm; mass 35 g), eluting with a cyclohexane/ethylacetate mixture (90/10 by volume) and then with a cyclohexane/ethylacetate mixture (60/40 by volume) and collecting 20-cm³ fractions. Thefractions containing the product were combined and then concentrated todryness under the conditions described above. 0.72 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylatewas obtained in the form of a viscous orange oil.

[3651] Mass spectrum: EI m/z=506 M⁺ m/z=415 C₂₃H₂₈ClN₂O₃ ⁺ m/z=300C₁₉H₂₆NO₂ ⁺ m/z=117 C₉H₉ ⁺ base peak

[3652] The ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared in the form of the monohydrochloride in Example 5.

EXAMPLE 294-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid

[3653] A mixture of 0.18 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidin-4-yl}carboxylatein 10 cm³ of dioxane, 10 cm³ of methanol and 0.99 cm³ of aqueous 5Nsodium hydroxide solution was stirred at a temperature in the region of75° C. for 17 hours. After cooling to about 45° C., the reaction mixturewas concentrated to dryness under a pressure gradually reduced to 9 kPaat a temperature in the region of 40° C. The pasty residue was taken upin 3 cm³ of chloroform/methanol/aqueous ammonia (12/3/0.5 by volume) andthe organic phase was then purified by chromatography under atmosphericpressure, on a column of silica gel (Bond Elut; particle size 70-200μ;diameter 2 cm; mass 5 g), eluting with a chloroform/methanol/aqueousammonia mixture (12/3/0.5 by volume).

[3654] The fractions containing the product were combined and thenconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 40° C. and the product was dried in an oven underreduced pressure (50 kPa) at a temperature in the region of 50° C. 0.15g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-aceticacid was obtained.

[3655]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.39 (mt: 2H);1.50 (mt: 2H); 1.61 (mt: 4H); 2.15 (broad s: 2H); from 2.30 to 2.60 (mt:4H); 2.63 (broad t, J=5.5 Hz: 2H); 3.12 (unresolved peak: 2H); 3.94 (s:3H); 4.06 (broad t, J=5.5 Hz: 2H); from 6.65 to 6.75 (mt: 3H); 7.36(broad s: 1H); 7.41 (broad d, J=9 Hz: 1H); 7.93 (d, J=9 Hz: 1H); 8.64(s: 1H).

Methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidin-4-yl}acetate

[3656] A mixture of 0.35 g of methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidin-4-yl}acetate,0.318 g of 1-(2-bromoethoxy)-3,5-difluorobenzene, 0.15 g of potassiumiodide and 0.62 g of potassium carbonate in 20 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was filtered through asilica cartridge (Bond Elut) and then rinsed with twice 2 cm³ ofacetonitrile. The organic phase was concentrated to dryness underreduced pressure (2.4 kPa) at a temperature in the region of 45° C.

[3657] The evaporation residue obtained was dissolved in 12 cm³ ofdimethylformamide and then purified by injection of 4 times 3 cm³ perchromatography onto an SCX silica gel cartridge (mass 1 g), eluting witha gradient of from pure methanol to a mixture of 4N ammoniacal methanol.The fractions containing the product were combined and then concentratedto dryness under compressed air at a temperature in the region of 45° C.The evaporation residue obtained was taken up in dichloromethane anddried in the open air for 48 hours and then oven-dried under reducedpressure (10 kPa) at a temperature in the region of 50° C. 0.195 g ofmethyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidin-4-yl}acetatewas obtained.

[3658]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, at a temperature of 353 K,δ in ppm): from 1.45 to 2.70 (mt: 16H); 3.17 (mt: 2H); 3.51 (s: 3H);3.96 (s: 3H); 4.24 (unresolved peak: 2H); from 6.60 to 6.70 (mt: 3H);7.38 (broad s: 1H); 7.42 (broad d, J=9 Hz: 1H); 7.94 (d, J=9 Hz: 1H);8.62 (broad s: 1H).

Methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidin-4-yl}acetate

[3659] A mixture of 17 g of tert-butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-cyanomethylpiperidine-1-carboxylatein 100 cm³ of aqueous 12N hydrochloric acid (concentrated to dryness)was gradually brought to a temperature in the region of 100° C. withstirring over 18 hours. The reaction mixture was concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 60° C.

[3660] The oil obtained was taken up in acetone and the precipitate wasfiltered off and washed with acetone. 20.4 g of{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidin-4-yl}acetic aciddihydrochloride were obtained in the form of a grayish solid melting at181° C. and becoming sticky. The above product was dissolved in 400 cm³of methanol and 10 cm³ of dry concentrated sulfuric acid, stirred andheated in the region of 100° C. for 1.5 hours. The reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 50° C.

[3661] The oil obtained was taken up in 300 cm³ of water with stirring,neutralized with sodium hydrogen carbonate, basified with potassiumcarbonate and extracted with ethyl acetate. The organic phase wasseparated out after settling has taken place, washed with water, driedover magnesium sulfate, filtered and then concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. Theaqueous phase was basified to pH 8 with aqueous 5N sodium hydroxidesolution and extracted with ethyl acetate, the phases were separated bysettling and the organic extracts were washed, dried with magnesiumsulfate and concentrated to dryness according to the conditionsdescribed above.

[3662] All the organic evaporation residues were combined and purifiedby chromatography under a pressure of 50 kPa of argon, on a column ofsilica gel (particle size 20-43μ; mass 200 g), eluting with adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume).The fractions containing the product were combined and concentrated todryness as under the above conditions. 7.6 g of methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidin-4-yl}acetatewere obtained in the form of orange-colored oil.

[3663] Mass spectrum: EI m/z=390 M⁺ m/z=207 C₁₁H₁₀ClNO⁺ m/z=184C₁₀H₁₈NO₂ ⁺

[3664] tert-Butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-cyanomethylpiperidine-1-carboxylate

[3665] A mixture of 30.58 g of tert-butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-methane-sulfonyloxymethylpiperidine-1-carboxylateand 15.1 g of potassium cyanide in 436 cm³ of dimethyl sulfoxide washeated with stirring at a temperature in the region of 100° C. for 48hours and was then stirred in the region of 20° C. for 24 hours. 2 000cm³ of ice-water were added to the reaction mixture, the suspension wasstirred for 1 hour at a temperature in the region of 20° C. and thenfiltered, and the filter cake was washed with 3 times 200 cm³ of waterand then dried in the open air.

[3666] The residue was purified by chromatography under a pressure of 50kPa of argon, on a column of silica gel (particle size 20-45μ; diameter9 cm; height 45 cm), eluting with a cyclohexane/ethyl acetate mixture(90/10 by volume). Fractions 40 to 100 were combined and concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of45° C. 19.25 g of tert-butyl4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-4-cyanomethylpiperidine-1-carboxylatewere obtained in the form of a yellow solid melting at 160° C.

[3667] Infra-red spectrum (KBr): 2968; 2924; 2235; 1684; 1622; 1505;1414; 1230; 1166; 1151; 826 and 738 cm⁻¹.

tert-Butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-methanesulfonyloxymethylpiperidine-1-carboxylate

[3668] A mixture of 24.8 g of tert-butyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-hydroxymethyl-piperidine-1-carboxylatein 400 cm³ of dichloromethane and 12.9 cm³ of triethylamine was cooledto about 0° C. with stirring and under an inert atmosphere.Methanesulfonyl chloride, dissolved beforehand in 125 cm³ ofdichloromethane, was added dropwise and the reaction mixture was thenstirred for 18 hours at a temperature in the region of 20° C. 200 cm³ ofwater were added to the reaction mass, followed by a further addition of3 000 cm³ of water. The phases were separated by settling and theaqueous phase was extracted with 200 cm³ of dichloromethane. The organicextracts were washed with 300 cm³ of aqueous sodium chloride solution,dried over sodium sulfate, filtered and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 45° C.30.6 g of tert-butyl4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-4-methanesulfonyloxymethylpiperidine-1-carboxylatewere obtained in the form of an orange-colored oil.

[3669] Mass spectrum: DCI m/z =507 MH⁺ m/z=431 M—CH₃SO₃ m/z=397 431-Clm/z=375 431-tBu m/z=331 431-BOC

[3670] The 1-(2-bromoethoxy)-3,5-difluorobenzene was prepared asdescribed in Example 16.

[3671] The tert-butyl4-[3-(3-chloro-6-methoxy-quinolin-4-yl)propyl]-4-hydroxymethylpiperidine-1-carboxylatewas prepared as described in Example 19.

EXAMPLE 30{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidin-4-yl}aceticacid

[3672] A mixture of 0.35 g of methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidin-4-yl}acetatein 10 cm³ of dioxane, 10 cm³ of methanol and 1.91 cm³ of aqueous SNsodium hydroxide solution was stirred at a temperature in the region of75° C. for 17 hours. After cooling to about 45° C., the reaction mixturewas concentrated to dryness under a pressure gradually reduced to 9 kPaat a temperature in the region of 40° C.

[3673] The pasty residue was taken up in 3 cm³ ofchloroform/methanol/aqueous ammonia (12/3/0.5 by volume) and the organicphase was then purified by chromatography under atmospheric pressure, ona column of silica gel (particle size 70-200μ; diameter 2 cm; mass 5 g),eluting with a chloroform/methanol/aqueous ammonia mixture (12/3/0.5 byvolume). The fractions containing the product were combined and thenconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 40° C. and the product was dried in an over underreduced pressure (50 Pa) at a temperature in the region of 50° C. 0.27 gof{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidin-4-yl}aceticacid was obtained.

[3674]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.39 (mt: 2H);1.50 (mt: 2H); 1.60 (mt: 4H); 2.15 (broad s: 2H); from 2.30 to 2.60 (mt:4H); 2.67 (t, J=6 Hz: 2H); 3.12 (unresolved peak: 2H); 3.93 (s: 3H);4.12 (t, J=6 Hz: 2H); 6.72 (mt: 1H); 7.11 (mt: 1H); 7.21 (mt: 1H); 7.37(broad s: 1H)^(.); 7.41 (broad d, J=9 Hz: 1H); 7.93 (d, J=9 Hz: 1H);8.64 (s: 1H).

[3675] Methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidin-4-yl}acetate

[3676] A mixture of 0.35 g of methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidin-4-yl}acetate,0.32 g of 2-(2-bromoethoxy)-1,4-difluorobenzene, 0.15 g of potassiumiodide and 0.62 g of potassium carbonate in 20 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was filtered through asilica cartridge (Bond Elut) and then rinsed with twice 2 cm³ ofacetonitrile. The organic phase was concentrated to dryness underreduced pressure (2.4 kPa) at a temperature in the region of 45° C.

[3677] The evaporation residue obtained in dissolved in 12 cm³ ofdimethylformamide and then purified by injection of 4 times 3 cm³ perchromatography onto an SCX silica gel cartridge (mass 1 g), eluting witha gradient of from pure methanol to a mixture of 4N ammoniacal methanol.The fractions containing the product were combined and then concentratedto dryness under compressed air at a temperature in the region of 45° C.The evaporation residue obtained was taken up in dichloromethane anddried in the open air for 48 hours and then oven-dried under reducedpressure (10 Pa) at a temperature in the region of 50° C. 0.38 g ofmethyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidin-4-yl}acetatewas obtained.

[3678]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.30 to1.65 (mt: 8H); 2.25 (broad s: 2H); from 2.30 to 2.60 (mt: 4H); 2.69 (mt:2H); 3.14 (mt: 2H); 3.47 (broad s: 3H); 3.95 (broad s: 3H); 4.12 (mt:2H); 6.72 (mt: 1H); 7.11 (mt: 1H); 7.21 (mt: 1H); 7.38 (broad s: 1H);7.43 (broad d, J=9 Hz: 1H); 7.94 (broad d, J=9 Hz: 1H); 8.66 (broad s:1H).

[3679] The 2-(2-bromoethoxy)-1,4-difluorobenzene was prepared asdescribed in Example 16.

[3680] The methyl{4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidin-4-yl}acetate wasprepared as described in Example 29.

EXAMPLE 31

[3681]1-(2-Cyclopentylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3682] A mixture of 0.4 g of ethyl1-(2-cyclopentylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.4 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 to2.5 kPa and at a temperature in the region of 45° C.

[3683] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (13/3/0.5). The fractions containing a precipitate werecombined, filtered and then washed with methanol. The solid obtained wasrecrystallized from 15 cm³ of boiling methanol, cooled, filtered, washedwith methanol and oven-dried under reduced pressure (10 Pa) in theregion of 20° C. The filtration liquors were combined and concentratedto dryness under reduced pressure (2 kPa) at a temperature in the regionof 40° C. The liquors, once concentrated to dryness, and the solidobtained above were combined to give 0.179 g of1-(2-cyclopentylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid in the form of a white solid.

[3684]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): 1.41 (mt: 2H); from 1.50 to 1.75 (mt: 8H); from1.90 to 2.05 (mt: 4H); 2.20 (broad d, J=14 Hz: 2H); from 2.75 to 2.90(mt: 4H); from 3.10 to 3.25 (mt: 1H); 3.16 (t, J=7 Hz: 2H); 3.29 (mt:2H); 3.50 (broad d, J=14 Hz: 2H); 3.99 (s: 3H); 7.47 (d, J=2.5 Hz: 1H);7.55 (dd, J=9 and 2.5 Hz: 1H); 8.06 (d, J=9 Hz: 1H); 8.98 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3685] A mixture of 0.5 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.253 g of (2-chloroethylthio)cyclopentane, 0.25 g of potassium iodideand 0.92 g of potassium carbonate in 15 cm³ of acetonitrile was stirredfor 18 hours at a temperature in the region of 70° C. After cooling toabout 20° C., the reaction mixture was filtered and then rinsed withtwice 3 cm³ of acetonitrile. The organic phase was concentrated todryness under reduced pressure (2.4 kPa) at a temperature in the regionof 45° C.

[3686] The evaporation residue obtained was dissolved in a mixture ofethyl acetate/40-60° C. petroleum ether (8/2 by volume) and was thenpurified by chromatography under atmospheric pressure, on a cartridge ofsilica gel (Bond Elut; particle size 70-200μ; mass 10 g), eluting with amixture of ethyl acetate/40-60° C. petroleum ether (8/2 by volume).Fractions 5 to 14 were combined and then concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. 0.43 gof ethyl4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3687]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.98 (t, J=7 Hz:3H); 1.36 (mt: 4H); from 1.40 to 1.70 (mt: 8H); from 1.80 to 2.00 (mt:6H); from 2.30 to 2.65 (mt: 6H); 3.02 (mt: 2H); 3.09 (mt: 1H); 3.92 (s:3H); 3.94 (q, J=7 Hz: 2H); 7.31 (broad s: 1H); 7.37 (broad d, J=9 Hz:1H); 7.94 (d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3688] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 321-(2-Cyclohexylethyl)-4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3689] A mixture of 0.2 g of ethyl1-(2-cyclohexyl-ethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 1.2 cm³ of aqueous SN sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 22 hours. After cooling to about 20° C., the reaction mixture wasevaporated under a pressure gradually reduced from 30 kPa to 2.5 kPa andat a temperature in the region of 45° C.

[3690] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (13/3/0.5). The fractions containing the product were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and dried in a desiccator (10 kPa). 0.14 g of1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3691]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): from 0.80 to 1.00 (mt: 2H); from 1.05 to 1.35(mt: 5H); from 1.40 to 1.75 (mt: 12H); 2.19 (broad d, J=14 Hz: 2H); 2.78(broad t, J=12.5 Hz: 2H); 3.07 (mt: 2H); 3.20 (broad t, J=6.5 Hz: 2H);3.45 (broad d, J=12.5 Hz: 2H); 4.00 (s: 3H); 7.52 (d, J=2.5 Hz: 1H);7.60 (dd, J=9 and 2.5 Hz: 1H); 8.10 (d, J=9 Hz: 1H); 9.10 (d, J=2 Hz:1H).

Ethyl1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3692] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.245 g of 1-bromo-2-cyclohexylethane, 0.18 g of potassium iodide and0.737 g of potassium carbonate in 15 cm³ of acetonitrile was stirred for18 hours at a temperature in the region of 70° C. After cooling to about20° C., the reaction mixture was concentrated to dryness under reducedpressure (5 kPa) at a temperature in the region of 40° C.

[3693] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200 μ; mass 12 g), eluting with a mixture of ethylacetate/40-60° C. petroleum ether (8/2 by volume). The fractionscontaining the product were combined and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.0.23 g of ethyl1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3694]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.84 (mt: 2H);0.98 (t, J=7 Hz: 3H); from 1.00 to 2.65 (mt: 25H); 3.02 (mt: 2H); 3.93(s: 3H); 3.95 (q, J=7 Hz: 2H); 7.31 (broad s: 1H); 7.35 (broad d, J=9Hz: 1H); 7.94 (d, J=9 Hz: 1H); 8.67 (broad s: 1H).

[3695] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 331-(2-Cyclohexylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3696] A mixture of 0.3 g of ethyl1-(2-cyclohexyl-thioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 1.7 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3697] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (13/3/0.5). The fractions containing the product were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and dried in a desiccator (10 kPa). 0.25 g of1-(2-cyclohexylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3698]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): from 1.15 to 1.35 (mt: 5H); from 1.50 to 1.75(mt: 8H); from 1.80 to 2.05 (mt: 3H); 2.20 (broad d, J=14 Hz: 2H); from2.65 to 2.90 (mt: 5H); 3.20 (broad t, J=7 Hz: 2H); 3.25 (mt: 2H); 3.50(broad d, J=12 Hz: 2H); 4.00 (s: 3H); 7.50 (d, J=2.5 Hz: 1H); 7.59 (dd,J=9 and 2.5 Hz: 1H); 8.09 (d, J=9 Hz: 1H); 9.07 (d, J=2.5 Hz: 1H).

Ethyl1-(2-cyclohexylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3699] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.23 g of 2-chloroethylthiocyclohexane, 0.18 g of potassium iodide and0.74 g of potassium carbonate in 15 cm³ of acetonitrile was stirred for18 hours at a temperature in the region of 70° C. After cooling to about20° C., the reaction mixture was concentrated to dryness under reducedpressure (5 kPa) at a temperature in the region of 40° C. Theevaporation residue was purified by chromatography under atmosphericpressure, on a cartridge of silica gel (Bond Elut; particle size70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60° C.petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.32 g of ethyl1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3700]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.97 (t, J=7 Hz:3H); from 1.05 to 1.70 (mt: 14H); from 1.75 to 2.00 (mt: 6H); from 2.25to 2.60 (mt: 6H); 2.62 (mt: 1H); 3.01 (mt: 2H); 3.91 (s: 3H); 3.94 (q,J=7 Hz: 2H); 7.30 (broad s: 1H); 7.37 (broad d, J=9 Hz: 1H); 7.93 (d,J=9 Hz: 1H); 8.66 (broad s: 1H).

[3701] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 344-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylicacid

[3702] A mixture of 0.1 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 0.6 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3703] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a mixture of dichloromethane/methanol/aqueous ammonia(40/5/0.5 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (13/3/0.5). The fractions containing the product were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and dried in a desiccator (10 Pa). 0.25 g of4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3704]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): from 1.50 to 1.75 (mt: 6H); from 1.85 to 2.05(mt: 2H); 2.19 (broad d, J=14 Hz: 2H); 2.60 (t, J=7.5 Hz: 2H); 2.81(broad t, J=12.5 Hz: 2H); 3.07 (mt: 2H); 3.20 (broad t, J=7.5 Hz: 2H);3.47 (broad d, J=12.5 Hz: 2H); 3.99 (s: 3H); from 7.15 to 7.35 (mt: 5H);7.51 (d, J=2.5 Hz: 1H); 7.59 (dd, J=9 and 2.5 Hz: 1H); 8.10 (d, J=9 Hz:1H); 9.08 (d, J=2 Hz: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylate

[3705] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.25 g of 1-bromo-3-phenylpropane, 0.181 g of potassium iodide and 0.74g of potassium carbonate in 15 cm³ of acetonitrile was stirred for 18hours at a temperature in the region of 70° C. After cooling to about20° C., the reaction mixture was concentrated to dryness under reducedpressure (5 kPa) at a temperature in the region of 40° C.

[3706] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of ₄₀° C. 0.1 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylatewas obtained.

[3707]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.97 (t, J=7 Hz:3H); from 1.25 to 2.00 (mt: 12H); from 2.25 to 2.70 (mt: 6H); 3.01 (mt:2H); 3.91 (s: 3H); 3.94 (broad q, J=7 Hz: 2H); 7.15 (mt: 3H); 7.24(broad t, J=7.5 Hz: 2H); 7.30 (broad s: 1H); 7.36 (broad d, J=9 Hz: 1H);7.93 (d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3708] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 351-[2-(2,5-Difluorophenylthio)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3709] A mixture of 0.26 g of ethyl1-[2-(2,5-difluorophenylthio)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 1.4 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C. The residue wastaken up in 5 cm³ of a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and was then purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 10 g), eluting with a mixture ofdichloromethane/methanol/aqueous ammonia (90/9/0.9 by volume) and thenwith a chloroform/methanol/aqueous ammonia mixture (77.5/19.5/3). Thefractions containing the product were combined, concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.and dried in a desiccator (10 kPa). 0.3 g of1-[2-(2,5-difluorophenylthio)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3710]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): from 1.50 to 1.75 (mt: 6H); 2.21 (broad d, J=14Hz: 2H); 2.89 (broad t, J=12.5 Hz: 2H); 3.16 (mt: 2H); from 3.25 to 3.50(mt: 4H); 3.54 (broad d, J=12.5 Hz: 2H); 3.99 (s: 3H); 7.14 (mt: 1H);7.30 (doubled triplet, J=9 and 5 Hz: 1H); 7.39 (mt: 1H); 7.47 (d, J=2.5Hz: 1H); 7.54 (dd, J=9 and 2.5 Hz: 1H); 8.07 (d, J=9 Hz: 1H); 8.97 (d,J=2 Hz: 1H).

Ethyl1-[2-(2,5-difluorophenylthio)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3711] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.324 g of 2-(2-bromoethylthio)-1,4-difluorobenzene, 0.181 g ofpotassium iodide and 0.74 g of potassium carbonate in 15 cm³ ofacetonitrile was stirred for 18 hours at a temperature in the region of70° C. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 40° C. The evaporation residue was purified bychromatography under atmospheric pressure, on a cartridge of silica gel(Bond Elut; particle size 70-200μ; mass 12 g), eluting with a mixture ofethyl acetate/40-60° C. petroleum ether (8/2 by volume).

[3712] The fractions containing the product were combined and thenconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. 0.27 g of ethyl1-[2-(2,5-difluorophenylthio)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3713]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.97 (t, J=7 Hz:3H); 1.31 (broad t, J=11 Hz: 2H); from 1.40 to 1.60 (mt: 4H); from 1.80to 2.00 (mt: 4H); from 2.35 to 2.70 (mt: 4H); 3.01 (mt: 2H); 3.07 (broadt, J=7 Hz: 2H); 3.91 (s: 3H); 3.94 (q, J=7 Hz: 2H); 7.00 (mt: 1H); 7.21(mt: 1H); 7.26 (mt: 1H); 7.30 (broad s: 1H); 7.37 (broad d, J=9 Hz: 1H);7.93 (d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3714] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

[3715] The 1-(2-bromoethylthio)-2,5-difluorobenzene was prepared asdescribed in Example 14.

EXAMPLE 361-[2-(2,5-Difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3716] A mixture of 0.38 g of ethyl1-[2-(2,5-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.1 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3717] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(90/9/0.9 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (77.5/19.5/3).

[3718] The fractions containing the product were combined, concentratedto dryness under reduced pressure (2 kPa) at a temperature in the regionof 40° C. and dried in a desiccator (10 kPa). 0.36 g of1-[2-(2,5-difluorophenoxy)ethyl]-4-(3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3719]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.32 (broad t,J=13 Hz: 2H); from 1.50 to 1.70 (mt: 4H); 1.96 (broad d, J=13 Hz: 2H);2.09 (broad t, J=11.5 Hz: 2H); 2.64 (t, J=6 Hz: 2H); 2.70 (broad d,J=11.5 Hz: 2H); 3.05 (very broad t, J=6.5 Hz: 2H); 3.96 (s: 3H); 4.13(t, J=6 Hz: 2H); 6.75 (mt: 1H); 7.14 (mt: 1H); 7.24 (mt: 1H); 7.34 (d,J=2.5 Hz: 1H); 7.41 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.69(broad s: 1H).

Ethyl1-[2-(2,5-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3720] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.30 g of 2-(2-bromoethoxy)-1,4-difluorobenzene, 0.181 g of potassiumiodide and 0.74 g of potassium carbonate in 15 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3721] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.4 g of ethyl1-[2-(2,5-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3722]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.97 (t, J=7 Hz:3H); 1.36 (broad t, J=11.5 Hz: 2H); from 1.40 to 1.60 (mt: 4H); from1.80 to 2.10 (mt: 4H); 2.61 (broad t, J=5.5 Hz: 2H); 2.69 (broad d, J=11Hz: 2H); 3.02 (mt: 2H); 3.92 (s: 3H); 3.94 (q, J=7 Hz: 2H); 4.09 (mt:2H); 6.71 (mt: 1H); 7.10 (mt: 1H); 7.19 (mt: 1H); 7.29 (broad s: 1H);7.37 (broad d, J=9 Hz: 1H); 7.93 (d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3723] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

[3724] The 2-(2-bromoethoxy)-1,4-difluorobenzene was prepared asdescribed in Example 16.

EXAMPLE 374-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[3725] A mixture of 0.42 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-phenoxy)ethyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.3 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3726] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(90/9/0.9 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (77.5/19.5/3). The fractions containing the product werecombined, concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. and dried in a desiccator (10 kPa).0.39 g of4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]-1-[2-(2,3,5-trifluoro-phenoxy)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3727]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.32 (very broadt, J=12.5 Hz: 2H); 1.60 (mt: 4H); 1.95 (broad d, J=12.5 Hz: 2H); 2.09(broad t, J=11 Hz: 2H); 2.64 (t, J=5.5 Hz: 2H); 2.70 (broad d, J=11 Hz:2H); 3.04 (very broad t, J=6 Hz: 2H); 3.96 (s: 3H); 4.16 (t, J=5.5 Hz:2H); from 6.95 to 7.15 (mt: 2H); 7.34 (d, J=2.5 Hz: 1H); 7.40 (dd, J=9and 2.5 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.69 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylate

[3728] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.33 g of 1-(2-bromoethoxy)-2,3,5-trifluorobenzene, 0.181 g of potassiumiodide and 0.74 g of potassium carbonate in 15 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3729] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g; volume 25 cm³), eluting with a mixture of ethylacetate/40-60° C. petroleum ether (8/2 by volume). The fractionscontaining the product were combined and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.0.43 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,3,5-trifluorophenoxy)ethyl]piperidine-4-carboxylatewas obtained.

[3730]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.98 (t, J=7 Hz:3H); 1.34 (broad t, J=11.5 Hz: 2H); from 1.45 to 1.60 (mt: 4H); from1.85 to 2.10 (mt: 4H); from 2.50 to 2.70 (mt: 4H); 3.02 (mt: 2H); 3.92(s: 3H); 3.94 (q, J=7 Hz: 2H); 4.14 (mt: 2H); 7.02 (mt: 2H); 7.30 (broads: 1H); 7.37 (broad d, J=9 Hz: 1H); 7.94 (d, J=9 Hz: 1H); 8.66 (broad s:1H).

[3731] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

[3732] The 1-(2-bromoethoxy)-2,3,5-trifluorobenzene was prepared asdescribed in Example 13.

EXAMPLE 384-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylicacid

[3733] A mixture of 0.16 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 1 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3734] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (13/3/0.5). The fractions containing the product were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and dried in a desiccator (10 kPa). 0.07 g of4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylicacid was obtained in the form of a white solid.

[3735]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): 0.85 (t, J=7 Hz: 3H); from 1.15 to 1.35 (mt: 8H);from 1.50 to 1.75 (mt: 8H); 2.19 (broad d, J=14 Hz: 2H); 2.78 (broad t,J=12.5 Hz: 2H); 3.02 (mt: 2H); 3.19 (broad t, J=7 Hz: 2H); 3.45 (broadd, J=12.5 Hz: 2H); 4.00 (s: 3H); 7.50 (d, J=2.5 Hz: 1H); 7.58 (dd, J=9and 2.5 Hz: 1H); 8.09 (d, J=9 Hz: 1H); 9.04 (d, J=2 Hz: 1H).

[3736] Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylate

[3737] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.23 g of 1-bromoheptane, 0.18 g of potassium iodide and 0.737 g ofpotassium carbonate in 15 cm³ of acetonitrile was stirred for 18 hoursat a temperature in the region of 70° C. After cooling to about 20° C.,the reaction mixture was concentrated to dryness under reduced pressure(5 kPa) at a temperature in the region of 40° C.

[3738] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (particle size70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60° C.petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.2 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylatewas obtained.

[3739]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.84 (t, J=7 Hz:3H); 0.98 (t, J=7 Hz: 3H); from 1.10 to 1.30 (mt: 8H); 1.33 (mt: 4H);from 1.40 to 1.60 (mt: 4H); 1.83 (broad t, J=11 Hz: 2H); 1.93 (broad d,J=13 Hz: 2H); 2.13 (mt: 2H); from 2.35 to 2.55 (mt: 2H); 3.01 (mt: 2H);3.89 (s: 3H); 3.94 (mt: 2H); 7.31 (broad s: 1H); 7.37 (broad d, J=9 Hz:1H); 7.94 (d, J=9 Hz: 1H); 8.67 (broad s: 1H).

[3740] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 394-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylicacid

[3741] A mixture of 0.39 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.3 cm³ of aqueous SN sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C. The residue wastaken up in 5 cm³ of a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and was then purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 10 g), eluting with adichloromethane/methanol/aqueous ammonia mixture (90/9/0.9 by volume)and then with a chloroform/methanol/aqueous ammonia mixture(77.5/19.5/3). The fractions containing the product were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and dried in a desiccator (10 kPa). 0.3 g of4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3742]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): from 1.50 to 1.75 (mt: 6H); 2.20 (broad d, J=14Hz: 2H); 2.87 (broad t, J=13 Hz: 2H); 3.16 (mt: 2H); 3.41 (s: 4H); 3.53(broad d, J=13 Hz: 2H); 4.00 (s: 3H); 7.25 (broad t, J=7.5 Hz: 1H); from7.30 to 7.45 (mt: 4H); 7.48 (d, J=2.5 Hz: 1H); 7.54 (dd, J=9 and 2.5 Hz:1H); 8.07 (d, J=9 Hz: 1H); 8.97 (d, J=2 Hz: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylate

[3743] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.28 g of 2-bromoethyl phenyl sulfide, 0.181 g of potassium iodide and0.74 g of potassium carbonate in 15 cm³ of acetonitrile was stirred for18 hours at a temperature in the region of 70° C. After cooling to about20° C., the reaction mixture was concentrated to dryness under reducedpressure (5 kPa) at a temperature in the region of 40° C.

[3744] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylatewas obtained.

[3745]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.97 (t, J=7 Hz:3H); 1.33 (broad t, J=12.5 Hz: 2H); from 1.45 to 1.65 (mt: 4H); from1.85 to 2.00 (mt: 4H); from 2.30 to 2.70 (mt: 4H); 3.01 (mt: 4H); 3.92(s: 3H); 3.94 (mt: 2H); 7.15 (mt: 1H); from 7.20 to 7.35 (mt: 5H); 7.37(broad d, J=9 Hz: 1H); 7.93 (d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3746] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 404-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-fluorophenylthio)ethyl]piperidine-4-carboxylicacid

[3747] A mixture of 0.2 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 1.1 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3748] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(90/9/0.9 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (77.5/19.5/3). The fractions containing the product werecombined, concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. and dried in a desiccator (10 kPa).0.18 g of4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]-1-[2-(3-fluorophenyl-thio)ethyl]piperidine-4-carboxylicacid was obtained.

[3749]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): from 1.50 to 1.75 (mt: 6H); 2.20 (broad d, J=14Hz: 2H); 2.89 (broad t, J=12.5 Hz: 2H); 3.18 (mt: 2H); from 3.25 to 3.45(mt: 4H); 3.54 (broad d, J=12.5 Hz: 2H); 3.99 (s: 3H); 7.05 (doubledtriplet, J=9 and 2.5 Hz: 1H); from 7.15 to 7.30 (mt: 2H); 7.38 (mt: 1H);7.48 (d, J=2.5 Hz: 1H); 7.55 (dd, J=9 and 2.5 Hz: 1H); 8.08 (d, J=9 Hz:1H); 9.00 (d, J=2 Hz: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylate

[3750] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.30 g of 3-fluoro-2-bromoethyl phenyl sulfide, 0.18 g of potassiumiodide and 0.74 g of potassium carbonate in 15 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3751] The evaporation residue was purified by chromatography underatmospheric pressure of argon, on a cartridge of silica gel (Bond Elut;particle size 70-200μ; mass 12 g), eluting with a mixture of ethylacetate/40-60° C. petroleum ether (8/2 by volume). The fractionscontaining the product were combined and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.0.22 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenylthioethyl)piperidine-4-carboxylatewas obtained.

[3752]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.98 (t, J=7 Hz:3H); 1.33 (broad t, J=12 Hz: 2H); from 1.45 to 1.65 (mt: 4H); from 1.85to 2.00 (mt: 4H); from 2.30 to 2.70 (mt: 4H); 3.02 (mt: 2H); 3.07 (t,J=6.5 Hz: 2H); 3.92 (s: 3H); 3.94 (q, J=7 Hz: 2H); 6.94 (broad t, J=8.5Hz: 1H); from 7.05 to 7.20 (mt: 2H); from 7.25 to 7.35 (mt: 2H); 7.37(broad d, J=9 Hz: 1H); 7.94 (d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3753] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

[3754] The 3-fluoro-2-bromoethyl phenyl sulfide was prepared accordingto the method described in Example 14.

EXAMPLE 411-[2-(3,4-Difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3755] A mixture of 0.38 g of ethyl1-[2-(3,4-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.1 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C. The residue wastaken up in 5 cm³ of a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and was then purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 10 g), eluting with a mixture ofdichloromethane/methanol/aqueous ammonia (90/9/0.9 by volume) and thenwith a chloroform/methanol/aqueous ammonia mixture (77.5/19.5/3). Thefractions containing the product were combined, concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.and dried in a desiccator (10 kPa). 0.3 g of1-[2-(3,4-difluoro-phenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)-propyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3756]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): from 1.50 to 1.75 (mt: 6H); 2.21 (broad d, J=14Hz: 2H); 2.96 (broad t, J=13 Hz: 2H); 3.19 (broad t, J=6.5 Hz: 2H); from3.50 to 3.65 (mt: 4H); 4.00 (s: 3H); 4.31 (t, J=5.5 Hz: 2H); 6.82 (mt:1H); 7.11 (mt: 1H); 7.35 (mt: 1H); 7.50 (d, J=2.5 Hz: 1H); 7.57 (dd, J=9and 2.5 Hz: 1H); 8.09 (d, J=9 Hz: 1H); 9.03 (d, J=2 Hz: 1H).

[3757] Ethyl1-[2-(3,4-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3758] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.3 g of 4-(2-bromoethoxy)-1,2-difluorobenzene, 0.18 g of potassiumiodide and 0.74 g of potassium carbonate in 15 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3759] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.4 g of ethyl1-[2-(3,4-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3760]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.98 (t, J=7 Hz:3H); 1.36 (broad t, J=12 Hz: 2H); from 1.45 to 1.65 (mt: 4H); 1.93(broad d, J=12 Hz: 2H); 2.00 (broad t, J=11.5 Hz: 2H); from 2.40 to 2.70(mt: 4H); 3.02 (mt: 2H); 3.92 (s: 3H); 3.94 (q, J=7 Hz: 2H); 3.99 (mt:2H); 6.73 (mt: 1H); 7.03 (mt: 1H); from 7.25 to 7.35 (mt: 2H); 7.37(broad d, J=9 Hz: 1H); 7.93 (d, J=9 Hz: 1H); 8.66 (broad s,: 1H).

4-(2-Bromoethoxy)-1,2-difluorobenzene

[3761] A mixture of 15 g of 3,4-difluorophenol, 23.5 g of potassiumcarbonate and 60 cm³ of 1,2-dibromoethane in 250 cm³ of acetonitrile wasstirred at a temperature in the region of 70° C. for 18 hours. Aftercooling to about 20° C., the reaction mixture was filtered throughCelite and then concentrated to dryness under reduced pressure (2 kPa)at a temperature in the region of 40° C. The residue obtained waspurified by chromatography under atmospheric pressure, on a column ofsilica gel (particle size 70-200μ; diameter 8 cm; mass 400 g), elutingwith 40-60° C. petroleum ether. The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) in the region of 40° C. 15.7 g of4-(2-bromoethoxy)-1,2-difluorobenzene were obtained in the form of anoil.

[3762] Infra-red spectrum (CCl₄): 1609; 1516; 1264; 1253; 1215; 1206;1162; 1019; 854 and 834 cm⁻¹.

[3763] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 424-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenoxyethyl)piperidine-4-carboxylicacid

[3764] A mixture of 0.39 of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenoxyethyl)piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.4 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3765] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a mixture of dichloromethane/methanol/aqueous ammonia(90/9/0.9 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (77.5/19.5/3). The fractions containing the product werecombined, concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. and dried in a desiccator (10 kPa).0.33 g of4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]-1-(2-phenoxyethyl)piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3766]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): 1.36 (broad t, J=12.5 Hz: 2H); from 1.50 to 1.70(mt: 4H); 1.96 (broad d, J=12.5 Hz: 2H); 2.08 (broad t, J=11.5 Hz: 2H);2.62 (t, J=6 Hz: 2H); 2.71 (broad d, J=11.5 Hz: 2H); 3.05 (broad t,J=6.5 Hz: 2H); 3.97 (s: 3H); 4.03 (t, J=6 Hz: 2H); from 6.85 to 7.00(mt: 3H); 7.29 (broad t, J=8 Hz: 2H); 7.35 (d, J=2.5 Hz: 1H); 7.40 (dd,J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.70 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenoxyethyl)piperidine-4-carboxylate

[3767] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.26 g of 2-bromoethyl phenyl ether, 0.181 g of potassium iodide and0.737 g of potassium carbonate in 15 cm³ of acetonitrile was stirred for18 hours at a temperature in the region of 70° C. After cooling to about20° C., the reaction mixture was concentrated to dryness under reducedpressure (5 kPa) at a temperature in the region of 40° C.

[3768] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-phenoxyethyl)piperidine-4-carboxylatewas obtained.

[3769]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.99 (t, J=7 Hz:3H); 1.37 (mt: 2H); from 1.45 to 1.65 (mt: 4H); from 1.85 to 2.10 (mt:4H); from 2.35 to 2.75 (mt: 4H); 3.03 (mt: 2H); 3.93 (s: 3H); 3.96 (q,J=7 Hz: 2H); 4.02 (mt: 2H); 6.90 (mt: 3H); 7.26 (broad t, J=7.5 Hz: 2H);7.32 (broad s: 1H); 7.38 (broad d, J=9 Hz: 1H); 7.95 (d, J=9 Hz: 1H);8.68 (broad s: 1H).

[3770] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 434-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-fluorophenoxy)ethyl]piperidine-4-carboxylicacid

[3771] A mixture of 0.415 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-fluorophenoxy)-ethyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.4 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3772] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(90/9/0.9 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (77.5/19.5/3). The fractions containing the product werecombined, concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. and dried in a desiccator (10 kPa).0.34 g of4-[3-(3-fluoro-6-methoxy-quinolin-4-yl)propyl]-1-[2-(3-fluorophenoxy)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3773]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CF₃COOD, δ in ppm): 1.34 (broad t, J=12.5 Hz: 2H); from 1.50 to 1.70(mt: 4H); 1.96 (broad d, J=12.5 Hz: 2H); 2.08 (broad t, J=11 Hz: 2H);2.63 (t, J=6 Hz: 2H); 2.70 (broad d, J=11 Hz: 2H); 3.05 (broad t, J=6.5Hz: 2H); 3.97 (s: 3H); 4.06 (t, J=6 Hz: 2H); from 6.70 to 6.90 (mt: 3H);from 7.25 to 7.40 (mt: 1H); 7.35 (d, J=2.5 Hz: 1H); 7.40 (dd, J=9 and2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.70 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-fluorophenoxy)ethyl]piperidine-4-carboxylate

[3774] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.281 g of 1-(2-bromoethoxy)-3-fluorobenzene, 0.181 g of potassiumiodide and 0.737 g of potassium carbonate in 15 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3775] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.43 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3-fluorophenoxy)ethyl]piperidine-4-carboxylatewas obtained.

[3776]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.98 (t, J=7 Hz:3H); 1.35 (broad t, J=12 Hz: 2H); from 1.45 to 1.65 (mt: 4H); 1.92(broad d, J=12 Hz: 2H); 2.00 (broad t, J=11.5 Hz: 2H); from 2.30 to 2.70(mt: 4H); 3.02 (mt: 2H); 3.91 (s: 3H); 3.94 (q, J=7 Hz: 2H); 4.01 (mt:2H); from 6.65 to 6.80 (mt: 3H); from 7.20 to 7.30 (mt: 1H); 7.28 (broads: 1H); 7.36 (broad d, J=9 Hz: 1H); 7.93 (d, J=9 Hz: 1H); 8.65 (broad s:1H).

1-(2-Bromoethoxy)-3-fluorobenzene

[3777] A mixture of 8.6 g of 3-fluorophenol, 15.3 g of potassiumcarbonate and 40.5 cm³ of 1,2-dibromoethane in 200 cm³ of acetonitrilewas stirred, under an inert atmosphere, at a temperature in the regionof 70° C. for 25 hours. After cooling to about 20° C., the suspensionwas filtered, the insoluble material was rinsed with 3 times 50-cm³ ofacetonitrile and the filtrate was then concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C.

[3778] The residue obtained was taken up in 50 cm³ of diethyl ether andthen filtered, and the filtration liquors were concentrated to drynessas under the previous conditions. The oil obtained by evaporation waspurified by chromatography under a pressure of 50 kPa of argon on acolumn of silica gel (particle size 20-45μ; diameter 4.5 cm; height 22cm), eluting with 40-60° C. petroleum ether. Fractions 8 to 60 werecombined and then concentrated to dryness under reduced pressure (2 kPa)in the region of 40° C. 7.67 g of 1-(2-bromoethoxy)-3-fluorobenzene wereobtained.

[3779] Infra-red spectrum (CCl₄): 1616; 1596; 1492; 1279; 1265; 1168;1140; 1025; 853; 834 and 679 cm⁻¹.

[3780] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 441-[2-(2,6-Difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3781] A mixture of 0.39 g of ethyl1-[2-(2,6-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.2 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C. The residue wastaken up in 5 cm³ of a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume) and was then purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 10 g), eluting with adichloromethane/methanol/aqueous ammonia mixture (90/9/0.9 by volume)and then with a chloroform/methanol/aqueous ammonia mixture(77.5/19.5/3). The fractions containing the product were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and dried in a desiccator (10 kPa). 0.3 g of1-[2-(2,6-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3782]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.33 (broad t,J=12.5 Hz: 2H); from 1.50 to 1.65 (mt: 4H); 1.91 (broad d, J=12.5 Hz:2H); 2.05 (broad t, J=11 Hz: 2H); 2.60 (t, J=6 Hz: 2H); 2.63 (mt: 2H);3.05 (mt: 2H); 3.97 (s: 3H); 4.16 (t, J=6 Hz: 2H); from 7.05 to 7.20(mt: 3H); 7.35 (d, J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H); 7.97(d, J=9 Hz: 1H); 8.70 (broad s: 1H).

Ethyl1-[2-(2,6-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3783] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.304 g of 1-(2-bromoethoxy)-3-fluorobenzene, 0.181 g of potassiumiodide and 0.74 g of potassium carbonate in 15 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of 70° C. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C.

[3784] The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.4 g of ethyl1-[2-(2,6-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3785]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.97 (t, J=7 Hz:3H); 1.26 (broad t, J=125 Hz: 2H); from 1.40 to 1.60 (mt: 4H); 1.88(broad d, J=12 Hz: 2H); 1.98 (broad t, J=11 Hz: 2H); from 2.30 to 2.65(mt: 4H); 3.00 (mt: 2H); 3.92 (s: 3H); 3.94 (mt: 2H); 4.11 (mt: 2H);from 6.95 to 7.10 (mt: 3H); 7.30 (broad s: 1H); 7.37 (broad d, J=9 Hz:1H); 7.93 (d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3786] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

[3787] The 1-(2-bromoethoxy)-3-fluorobenzene was prepared according tothe method described in Example 15.

EXAMPLE 451-[2-(2,3-Difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid

[3788] A mixture of 0.42 g of ethyl1-[2-(2,3-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 2.4 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 17 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under a pressure gradually reduced from 30 kPato 2.5 kPa and at a temperature in the region of 45° C.

[3789] The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and was then purified by chromatography under atmospheric pressure, on acartridge of silica gel (Bond Elut; particle size 70-200μ; mass 10 g),eluting with a dichloromethane/methanol/aqueous ammonia mixture(90/9/0.9 by volume) and then with a chloroform/methanol/aqueous ammoniamixture (77.5/19.5/3). The fractions containing the product werecombined, concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. and dried in a desiccator (10 kPa).0.32 g of1-[2-(2,3-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3790]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.34 (broad t,J=12.5 Hz: 2H); from 1.50 to 1.70 (mt: 4H); 1.96 (broad d, J=12.5 Hz:2H); 2.09 (broad t, J=11.5 Hz: 2H); 2.65 (t, J=6 Hz: 2H); 2.71 (broad d,J=11.5 Hz: 2H); 3.05 (mt: 2H); 3.97 (s: 3H); 4.16 (t, J=6 Hz: 2H); from6.90 to 7.20 (mt: 3H); 7.34 (d, J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz:1H); 7.97 (d, J=9 Hz: 1H); 8.70 (broad s: 1H).

Ethyl1-[2-(2,3-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate

[3791] A mixture of 0.4 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.3 g of 1-(2-bromoethoxy)-2,3-difluorobenzene, 0.181 g of potassiumiodide and 0.74 g of potassium carbonate in 15 cm³ of acetonitrile wasstirred for 18 hours at a temperature in the region of .70° C. Aftercooling to about 20° C., the reaction mixture was concentrated todryness under reduced pressure (5 kPa) at a temperature in the region of40° C. The evaporation residue was purified by chromatography underatmospheric pressure, on a cartridge of silica gel (Bond Elut; particlesize 70-200μ; mass 12 g), eluting with a mixture of ethyl acetate/40-60°C. petroleum ether (8/2 by volume). The fractions containing the productwere combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 0.43 g of ethyl1-[2-(2,3-difluorophenoxy)ethyl]-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas obtained.

[3792]¹H NMR Spectrum (500 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.99 (mt: 3H);1.34 (mt: 2H); from 1.40 to 1.60 (mt: 4H); 1.93 (broad d, J=12.5 Hz:2H); from 1.95 to 2.10 (mt: 2H); from 2.45 to 2.70 (mt: 4H); 3.02 (mt:2H); 3.93 (s: 3H); 3.95 (mt: 2H); 4.12 (mt: 2H); from 6.85 to 7.05 (mt:2H); 7.09 (mt: 1H); 7.31 (broad s: 1H); 7.37 (broad d, J=9 Hz: 1H); 7.94(d, J=9 Hz: 1H); 8.66 (broad s: 1H).

[3793] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

[3794] The 1-(2-bromoethoxy)-2,3-difluorobenzene was prepared asdescribed in Example 17.

EXAMPLE 464-[3-(3-Fluoroquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid

[3795] A mixture of 1.29 g of ethyl4-[3-(3-fluoro-quinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylatein 65 cm³ of dioxane, 65 cm³ of methanol and 8 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 20 hours. 8 cm³ of aqueous 5N sodium hydroxide solution were addedto the reaction mixture, which was stirred in the region of 70° C. for afurther 6 hours. After cooling to about 20° C., the reaction mass wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 50° C. The residue was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 6 cm; height 30 cm), eluting with a chloroform/methanol/aqueousammonia mixture (12/3/0.5 by volume) and collecting 100-cm³ fractions.Fractions 8 to 24 were combined and concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. Thewhite solid was taken up in 60 cm³ of diisopropyl ether and stirred for18 hours at a temperature in the region of 20° C. The suspension wasfiltered, washed with 3 times 15 cm³ of diisopropyl ether, spin-filteredand then dried under reduced pressure (10 kPa) at about 50° C. 0.8 g of4-[3-(3-fluoroquinolin-4-yl)propyl]-1-[2-(thien-2-yl)-thioethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 180° C.

[3796]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.27 (mt: 2H);1.56 (mt: 4H); from 1.85 to 2.05 (mt: 4H); 2.44 (broad t, J=7 Hz: 2H);2.57 (mt: 2H); 2.90 (broad t, J=7 Hz: 2H); 3.06 (unresolved peak: 2H);7.04 (dd, J=5.5 and 3.5 Hz: 1H); 7.17 (dd, J=3.5 and 1.5 Hz: 1H); 7.60(dd, J=5.5 and 1.5 Hz: 1H); 7.71 (broad t, J=7.5 Hz: 1H); 7.77 (broad t,J=7.5 Hz: 1H); 8.08 (broad d, J=7.5 Hz: 1H); 8.15 (broad d, J=7.5 Hz:1H); 8.89 (d, J=1.5 Hz: 1H).

Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylate

[3797] A mixture of 1.8 g of ethyl1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylatemonohydrochloride, 0.48 cm³ of thiophene-2-thiol, 2.8 g of potassiumcarbonate and 0.75 g of potassium iodide in 200 cm³ of anhydrousacetonitrile was stirred under an inert atmosphere for 18 hours at atemperature in the region of 70° C. After cooling to about 20° C., thesuspension was filtered, washed with 3 times 30 cm³ of acetonitrile andthe filtrate was then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 50° C. The evaporation residuewas purified by chromatography under atmospheric pressure, on a columnof silica gel (particle size 20-45μ; diameter 6 cm; height 30 cm),eluting with ethyl acetate and collecting 50-cm³ fractions. Fractions 25to 52 were combined and then concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. 1.3 g of ethyl4-[3-(3-fluoroquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylatewere obtained in the form of a viscous orange-colored oil.

[3798]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.99 (t, J=7 Hz:3H); 1.34 (very broad t, J=13 Hz: 2H); 1.56 (mt: 4H); from 1.85 to 2.00(mt: 4H); 2.45 (broad t, J=7 Hz: 2H); 2.59 (broad d, J=11.5 Hz: 2H);2.90 (broad t, J=7 Hz: 2H); 3.07 (broad t, J=6.5 Hz: 2H); 3.95 (q, J=7Hz: 2H); 7.04 (dd, J=5.5 and 3.5 Hz: 1H); 7.17 (dd, J=3.5 and 1.5 Hz:1H); 7.60 (dd, J=5.5 and 1.5 Hz: 1H); 7.70 (broad t, J=7.5 Hz: 1H); 7.77(doubled triplet, J=7.5 and 1.5 Hz: 1H); 8.08 (broad d, J=7.5 Hz: 1H);8.13 (broad d, J=7.5 Hz: 1H); 8.89 (d, J=1 Hz: 1H).

Ethyl1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylatehydrochloride

[3799] 1.2 cm³ of thionyl chloride in 5 cm³ of dichloromethane wereadded to a solution of 1.55 g of ethyl4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(2-hydroxy-ethyl)piperidine-4-carboxylatein 35 cm³ of dichloromethane, with stirring at a temperature in theregion of 20° C. After stirring for 42 hours at a temperature in theregion of 20° C., the reaction mixture was concentrated to dryness underreduced pressure (1.2 kPa) at about 50° C. The foam obtained was takenup in 3 times 100 cm³ of cyclohexane, concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. andoven-dried under reduced pressure (10 kPa) at a temperature in theregion of 20° C. 1.8 g of ethyl1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylatemonohydrochloride were obtained in the form of a cream-colored solid.

[3800]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.03 (t, J=7 Hz:3H); from 1.45 to 2.10 (mt: 6H); 2.16 (broad d, J=14 Hz: 2H); from 2.70to 3.00 (mt: 2H); 3.12 (mt: 2H); from 3.40 to 3.55 (mt: 4H); from 3.95to 4.10 (mt: 4H); 7.72 (broad t, J=7.5 Hz: 1H); 7.79 (broad t, J=7.5 Hz:1H); 8.09 (broad d, J=7.5 Hz: 1H); 8.18 (broad d, J=7.5 Hz: 1H); 8.92(broad s: 1H); from 10.10 to 10.35 (unresolved peak: 1H).

Ethyl4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylate

[3801] 1.14 cm³ of 2-iodoethanol and 1.9 g of potassium carbonate wereadded to a solution of 4.4 g of ethyl4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate in 100 cm³of anhydrous acetonitrile, with vigorous stirring and under an inertatmosphere. The reaction mixture was stirred for 18 hours in the regionof 20° C., filtered and washed with 3 times 30 cm³ of acetonitrile. Thefiltrate was concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 50° C. The evaporation residue was purifiedby chromatography under atmospheric pressure, on a column of silica gel(particle size 20-45μ; diameter 5 cm; height 32 cm), eluting withdichloromethane/methanol/aqueous ammonia (40/5/0.5 by volume) andcollecting 100-cm³ fractions. Fractions 8 to 12 were combined and thenconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. 3.5 g of ethyl4-[3-(3-fluoroquinolin-4-yl)-propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylatewere obtained in the form of a viscous orange-colored oil.

[3802]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.99 (t, J=7 Hz:3H); 1.36 (mt: 2H); 1.57 (mt: 4H); from 1.85 to 2.05 (mt: 4H); 2.29 (t,J=6.5 Hz: 2H); 2.61 (d mt, J=12 Hz: 2H); 3.08 (broad t, J=6 Hz: 2H);3.45 (mt: 2H); 3.96 (q, J=7 Hz: 2H); 4.31 (t, J=5.5 Hz: 1H); 7.70 (broadt, J=7.5 Hz: 1H); 7.77 (doubled triplet, J=7.5 and 1.5 Hz: 1H); 8.08(dd, J=7.5 and 1.5 Hz: 1H); 8.14 (dd, J=7.5 and 1.5 Hz: 1H); 8.89 (d,J=1 Hz: 1H).

Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate

[3803] 50 cm³ of a solution of hydrogen chloride in dioxane at aconcentration of 4M were added cautiously to a solution of 8.7 g ofethyl4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylatein 150 cm³ of anhydrous dioxane, and the temperature was maintainedbelow 30° C. during the addition. After stirring for 18 hours in theregion of 20° C., the suspension was diluted with 250 cm³ of diethylether, filtered and washed with 5 times 50 cm³ of diethyl ether, and thesolid was dried in a desiccator under reduced pressure (2 kPa) and at atemperature in the region of 20° C. The solid was taken up in 50 cm³ ofwater and aqueous 5N sodium hydroxide solution was added so that the pHwas at about 10, and the mixture was then extracted with 5 times 100 cm³of diethyl ether. The organic phases were combined, dried over magnesiumsulfate, taken up with plant charcoal (3S), filtered and concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of50° C. 4.7 g of ethyl4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate wereobtained in the form of a viscous orange-colored oil.

[3804] Mass spectrum: EI m/z=344 M⁺ m/z=288 C₁₇H₁₉FNO₂ ⁺. m/z=184C₁₀H₁₈NO_(2+.) base peak m/z=161 C₁₀H₈FN⁺

Ethyl4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate

[3805] 17.7 g of ethyl4-allyl-1-(tert-butyloxy-carbonyl)piperidine-4-carboxylate in 200 cm³ oftetrahydrofuran were cooled to a temperature in the region of −30° C.and 135 cm³ of a 0.5M solution of 9-borabicyclo-[3.3.1]nonane intetrahydrofuran were added with stirring and under an inert atmosphere.After the addition, the temperature of the mixture was returned to about20° C. and the mixture was stirred for 2 hours. 14.8 g of3-fluoro-4-iodoquinoline in 430 cm³ of tetrahydrofuran, 1.3 g ofpalladium diphenylphosphinoferrocene chloride and 29.8 g of tribasicpotassium phosphate were added. The reaction mixture was then heated ata temperature in the region of 70° C. for 20 hours. After cooling to atemperature in the region of 20° C., the reaction mass was filtered andwashed with 3 times 100 cm³ of tetrahydrofuran. The filtrate wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The evaporation residue was taken up in 500 cm³of diethyl ether, the insoluble material was washed with 3 times 100 cm³of diethyl ether and the filtrate was concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. Theoil obtained was purified by chromatography under atmospheric pressure,on a column of silica gel (particle size 20-45μ; diameter 6 cm; height45 cm), eluting with a dichloromethane/ethyl acetate mixture (90/10 byvolume) and collecting 120-cm³ fractions. Fractions 30 to 76 werecombined and then concentrated to dryness under the same conditions asabove. 13.7 g of ethyl4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylatewere obtained in the form of a viscous orange-colored oil.

[3806] Mass spectrum: EI m/z =444 M^(+.) m/z=388 [M-tBu]^(+.) m/z=343[M-BOC]⁺ m/z=288 C₁₇H₁₉FNO₂ ^(+.) m/z=184 C₁₀H₈NO₂ ^(+.) m/z=161C₁₀H₈FN⁺ m/z=57 C₄H₉ ⁺

3-Fluoro-4-iodoquinoline

[3807] 17.3 cm³ of diisopropylamine in 650 cm³ of tetrahydrofuran werecooled to a temperature in the region of −75° C. and 76 cm³ of a 1.6Msolution of butyl lithium in hexane were added, with stirring and underan inert atmosphere, while maintaining the temperature at about −70° C.After stirring for 20 minutes at a temperature in the region of −75° C.,a solution of 11.9 g of 3-fluoroquinoline in 200 cm³ of tetrahydrofuranwas added. The solution obtained was stirred for a further 4 hours at−75° C., followed by addition of a solution of 32.2 g of double-sublimediodine in 150 cm³ of tetrahydrofuran. After stirring for 2 hours at atemperature in the region of −40° C., the reaction mixture washydrolyzed with 200 cm³ of a tetrahydrofuran/water mixture (90/10 byvolume) and then with 200 cm³ of saturated sodium chloride solution. Inthe region of 20° C., the mixture was diluted with 300 cm³ of ethylacetate and washed with twice 250 cm³ of saturated sodium chloridesolution. The organic phase was dried over magnesium sulfate, filteredand concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 50° C. The residue obtained was purified bychromatography under atmospheric pressure, on a column of silica gel(particle size 20-45μ; diameter 10 cm; height 30 cm), eluting withdichloromethane and collecting 100-cm³ fractions. Fractions 45 to 80were combined and then concentrated to dryness under reduced pressure (2kPa) at a temperature in the region of 40° C. 15.1 g of3-fluoro-4-iodoquinoline were obtained in the form of a cream-coloredsolid melting at 110° C.

[3808] Mass spectrum: EI m/z =273 M^(+.) base peak m/z =146 M-I]⁺

3-Fluoroquinoline

[3809] 23.5 g of 3-aminoquinoline and 12.1 g of sodium nitrite in 20 cm³of distilled water were added cautiously to 100 cm³ of tetrafluoroboricacid cooled to about 0° C., with vigorous stirring, and the reactionmixture was thus stirred for 30 minutes. The suspension was filtered,spin-filtered, washed with 3 times 30 cm³ of ice-cold tetrafluoroboricacid, 50 cm³ of ice-cold ethanol and 4 times 30 cm³ of diethyl ether.The solid was dried in a desiccator (2 kPa) in the region of 20° C. andthen taken up in 200 cm³ of toluene and heated at a temperature in theregion of 90° C. for 1 hour with stirring. After cooling to about 20°C., the phases of the reaction mass were separated by settling and theinsoluble oil was washed with 3 times 100 cm³ of toluene and taken up in110 cm³ of water, which was basified by slow addition of sodiumhydrogen-carbonate so that the pH was at about 8. The aqueous phase wasextracted with 5 times 100 cm³ of diethyl ether and the organic phaseswere combined, washed with twice 50 cm³ of water, dried over magnesiumsulfate and taken up with vegetable charcoal (3S), filtered andconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 45° C. The oil was taken up in 50 cm³ of a 40-60° C.petroleum ether/ethyl acetate mixture (90/10 by volume) and theinsoluble material was filtered off, rinsed with twice 25 cm³ of a40-60° C. petroleum ether/ethyl acetate mixture (90/10 by volume) anddried in a desiccator under reduced pressure (2 kPa) at a temperature inthe region of 20° C. The filtrate was concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. Theresidue obtained was purified by chromatography under atmosphericpressure, on a column of silica gel (particle size 20-45μ; diameter 5cm; height 45 cm), eluting with a 40-60° C. petroleum ether/ethylacetate mixture (90/10 by volume) and collecting 100-cm³ fractions.Fractions 20 to 31 were combined and then concentrated to dryness underreduced pressure (2 kPa) at a temperature in the region of 40° C. 13 gof 3-fluoroquinoline were obtained in the form of a colorless liquid.

[3810] Mass spectrum: EI m/z =147 M^(+.) base peak m/z=127 [M-HF]^(+.)m/z=120 [M-HCN]⁺

[3811] The ethyl4-allyl-1-(tert-butoxycarbonyl)-piperidine-4-carboxylate was prepared asdescribed in Example 1.

EXAMPLE 47

[3812] Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(pyridin-2-yloxy)ethyl]piperidine-4-carboxylatewas prepared in the form of a viscous colorless oil.

[3813]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.04 (t, J=7 Hz:3H); 1.39 (very broad t, J=12 Hz: 2H); 1.51 (mt: 2H); 1.68 (mt: 2H);from 1.90 to 2.15 (mt: 4H); 2.60 (t, J=6 Hz: 2H); 2.70 (broad d, J=12Hz: 2H); 3.16 (broad t, J=7.5 Hz: 2H); 3.95 (s: 3H); 3.99 (q, J=7 Hz:2H); 4.31 (t, J=6 Hz: 2H); 6.78 (d, J=8 Hz: 1H); 6.96 (broad dd, J=7.5and 5 Hz: 1H); 7.37 (d, J=2.5 Hz: 1H); 7.45 (dd, J=9 and 2.5 Hz: 1H);7.69 (ddd, J=8-7.5 and 2 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.14 (broad dd,J=5 and 2 Hz: 1H); 8.67 (s: 1H).

4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyridin-2-yloxy)ethyl]piperidine-4-carboxylicacid

[3814] A mixture of 0.12 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyridin-2-yloxy)-ethyl]piperidine-4-carboxylatein 5 cm³ of dioxane, 5 cm³ of methanol and 1 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 21 hours. After cooling to about 20° C., the reaction mass wasconcentrated to dryness under reduced pressure (5 kPa) at a temperaturein the region of 60° C. The residue was taken up in 5 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and then purified by chromatography under atmospheric pressure, on acolumn of silica gel (particle size 70-200μ; diameter 1.5 cm; mass 20g), eluting with a dichloromethane/methanol/aqueous ammonia mixture(40/5/0.5 by volume). The fractions containing the product were combinedand concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. The foam was taken up in 2 cm³ ofmethanol, filtered, washed with 1 cm³ of methanol and 2 cm³ of diethylether and then oven-dried under reduced pressure (10 kPa) at about 50°C. 0.115 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(pyridin-2-yloxy)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid melting at about 70° C.and becoming sticky.

[3815]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.20 to1.80 (mt: 6H); 1.98 (very broad d, J=13.5 Hz: 2H); 2.09 (very broad t,J=11 Hz: 2H); 2.60 (t, J=6 Hz: 2H); 2.67 (mt: 2H); 3.16 (mt: 2H); 3.98(s: 3H); 4.32 (t, J=6 Hz: 2H); 6.80 (d, J=8 Hz: 1H); 6.96 (ddd, J=7.5-5and 1 Hz: 1H); 7.39 (broad s: 1H); 7.45 (dd, J=9 and 2.5 Hz: 1H); 7.70(ddd, J=8-7.5 and 2 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.16 (broad dd, J=5and 2 Hz: 1H); 8.67 (s: 1H).

EXAMPLE 484-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylicacid

[3816] A mixture of 0.07 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 0.9 cm³ of aqueous 5N sodiumhydroxide solution was maintained at a temperature in the region of 70°C. for 4 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue was chromatographed underatmospheric pressure, on a column of silica gel (particle size 70-200μ;mass 10 g), eluting with a dichloromethane/methanol/aqueous ammoniamixture (40/5/0.5 by volume). Fractions 10 to 15 were combined and thenconcentrated to dryness under the same conditions as above. 0.04 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]-piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3817]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.20 to2.60 (mt: 12H); 2.66 (mt: 2H); 3.03 (t, J=7 Hz: 2H); 3.93 (s: 3H); 6.38(mt, J_(HF)=48 Hz: 1H); 7.05 (mt: 1H); from 7.20 to 7.40 (mt: 2H); 7.52(dd, J=9 and 2.5 Hz: 1H); 7.56 (d, J=2.5 Hz: 1H); 8.04 (d, J=9 Hz: 1H);8.75 (broad s: 1H); from 12.30 to 12.70 (broad unresolved peak: 1H).

Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]-piperidine-4-carboxylate

[3818] 0.1 cm³ of diethylaminosulfur trifluoride was added to a solutionof 0.25 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylatein 10 cm³ of dichloromethane, with stirring and under an inertatmosphere, at a temperature in the region of 5° C. After stirring for 7hours at a temperature in the region of 20° C., saturated sodiumhydrogen carbonate solution was added to the reaction mixture. Theaqueous phase was extracted with dichloromethane. The organic phase wasdried over magnesium sulfate, filtered and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.The residue obtained was purified by chromatography under atmosphericpressure, on a column of silica gel (particle size 70-200μ; mass: 15 g),eluting with 60 cm³ of dichloromethane, then with 45 cm³ of a mixture ofethyl acetate/dichloromethane (1/9 by volume), then with 30 cm³ of amixture of ethyl acetate/dichloromethane (2/8 by volume) and then with210 cm³ of a mixture of ethyl acetate/dichloromethane (3/7 by volume)and then with ethyl acetate. Fractions 24 to 26 were combined and thenconcentrated to dryness according to the same conditions as above. 0.08g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylatewas obtained in the form of a thick yellow oil.

[3819]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.20 to2.60 (mt: 12H); from 2.55 to 2.75 (mt: 2H); 3.11 (t, J=7 Hz: 2H); 3.54(s: 3H); 3.93 (s: 3H); 6.36 (mt, J_(HF)=48 Hz: 1H); 7.05 (mt: 1H); from7.15 to 7.35 (mt: 2H); from 7.45 to 7.55 (mt: 2H); 8.03 (d, J=9 Hz: 1H);8.75 (s: 1H).

Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(2,5-difluorophenylthio)ethyl]-piperidine-4-carboxylate

[3820] A mixture of 1.75 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatedihydrochloride, 0.95 g of 2-(2-bromoethylthio)-1,4-difluorobenzene,0.622 g of potassium iodide and 3.11 g of potassium carbonate in 30 cm³of acetonitrile and 20 cm³ of dimethylformamide was heated with stirringfor 18 hours at a temperature in the region of 85° C. After cooling toabout 20° C., the reaction mixture was filtered through Celite and thefiltrate was then concentrated to dryness under reduced pressure (2 kPa)at a temperature in the region of 40° C. The residue obtained was takenup in water and diethyl ether. The organic phase was dried overmagnesium sulfate, filtered and then concentrated to dryness as above.The residue obtained was purified by chromatography under atmosphericpressure, on a column of silica gel (particle size 70-200μ; diameter 4cm), eluting with a dichloromethane/methanol mixture (97.5/2.5 byvolume). The fractions containing the product were combined and thenconcentrated to dryness according to the same conditions as above. 0.6 gof methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylatewas obtained.

[3821]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.20 to2.15 (mt: 10H); from 2.45 to 2.55 (mt: 2H); 2.64 (mt: 2H); 3.12 (t, J=7Hz: 2H); 3.47 (s: 3H); 3.87 (s: 3H); 5.41 (mt: 1H); 6.10 (unresolvedpeak: 1H); 7.04 (mt: 1H); from 7.15 to 7.35 (mt: 2H); 7.45 (dd, J=9 and2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.13 (very broad d, J=2.5 Hz: 1H);8.66 (s: 1H).

[3822] The 2-(2-bromoethylthio)-1,4-difluorobenzene may be obtained byapplying the method described in Example 14.

[3823] The methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-4-carboxylatewas prepared in Example 49.

EXAMPLE 494-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid

[3824] A mixture of 0.15 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 1 cm³ of aqueous 5N sodiumhydroxide solution was maintained at a temperature in the region of 70°C. for 4 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue was chromatographed under anatmospheric pressure of 60 kPa, on a Bond Elut of 60 cm³ of silica gel(particle size 70-200μ; mass 25 g), eluting with 60 cm³ of adichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)and then with a dichloromethane/methanol/aqueous ammonia mixture (40/5/2by volume). The fractions containing the expected product were combinedand then concentrated to dryness according to the same conditions asabove. 0.04 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3825]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.20 to2.40 (mt: 10H); 2.65 (t, J=6 Hz: 2H); 2.72 (mt: 2H); 3.93 (s: 3H); 4.03(t, J=6 Hz: 2H); 6.37 (mt, J_(HF)=48 Hz: 1H); 6.75 (mt: 1H); 7.14 (mt:1H); 7.25 (mt: 1H); 7.52 (dd, J=9 and 2.5 Hz: 1H); 7.56 (d, J=2.5 Hz:1H); 8.03 (d, J=9 Hz: 1H); 8.75 (d, J=1 Hz: 1H).

Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenoxy)ethyl]-piperidine-4-carboxylate

[3826] 0.2 cm³ of diethylaminosulfur trifluoride was added to a solutionof 0.5 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylatein 20 cm³ of dichloromethane, with stirring and under an inertatmosphere, at a temperature in the region of 3° C. After stirring for 7hours at a temperature in the region of 20° C., saturated sodiumhydrogencarbonate solution was added to the reaction mixture. Theaqueous phase was extracted with dichloromethane. The organic phase wasdried over magnesium sulfate, filtered and then concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.The residue obtained was purified by chromatography under atmosphericpressure, on a column of silica gel (particle size 70-200μ; diameter 1.5cm; mass: 15 g), eluting with a mixture of ethyl acetate/petroleum ether(40-60° C.) (8/2 by volume). Fractions 9 to 11 were combined and thenconcentrated to dryness under the above conditions. 0.21 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylatewas obtained in the form of a thick yellow oil.

[3827] Mass spectrum: DCI m/z=551 MH⁺ Presence of an impurity m′=532.

Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)hydroxypropyl]-1-[2-(2,5-difluorophenoxy)ethyl]-piperidine-4-carboxylate

[3828] A mixture of 1.55 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-hydroxypropyl]piperidine-4-carboxylate,1.03 g of 1-(2-bromoethoxy)-2,5-difluorobenzene, 0.65 g of potassiumiodide and 2.7 g of potassium carbonate in 30 cm³ of acetonitrile and 20cm³ of dimethylformamide was heated with stirring at a temperature inthe region of 85° C. for 17 hours. After cooling to a temperature in theregion of 20° C., the suspension was filtered through Celite and thefiltrate was concentrated to dryness under reduced pressure (2 kPa) inthe region of 40° C.

[3829] The evaporation residue was taken up in dichloromethane andwater. The organic phase was dried over magnesium sulfate, filtered andconcentrated to dryness as under the above conditions. The residue waspurified by chromatography under atmospheric pressure, on a column ofsilica gel (particle size 70-200μ; diameter 4 cm), eluting with amixture of dichloromethane/methanol (97/3 by volume). The fractionscontaining the product were combined and then concentrated to drynessunder reduced pressure (2 kPa), at a temperature in the region of 40° C.and under the same conditions as above. 0.5 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)hydroxypropyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylatewas obtained.

[3830]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.20 to2.20 (mt: 10H); from 2.60 to 2.80 (mt: 2H); 2.64 (t, J=6 Hz: 2H); 3.48(s: 3H); 3.88 (s: 3H); 4.12 (t, J=6 Hz: 2H); 5.40 (mt: 1H); 6.10 (broads: 1H); 6.74 (mt: 1H); 7.13 (mt: 1H); 7.24 (mt: 1H); 7.44 (dd, J=9 and2.5 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.14 (d, J=2.5 Hz: 1H); 8.66 (s: 1H).

[3831] Methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)hydroxypropyl]piperidine-4-carboxylate

[3832] A mixture of 2.95 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)hydroxypropyl]-(tert-butyloxycarbonyl)piperidine-carboxylateand 2.3 cm³ of sulfuric acid in 100 cm³ of methanol was heated at atemperature in the region of 80° C. for 1 and a half hours. Aftercooling, the reaction mixture was concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. The residuewas taken up in 10 cm³ of water, basified to pH=11 with saturated sodiumbicarbonate solution and then with saturated sodium carbonate solutionand concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. The residue obtained was purified bychromatography under atmospheric pressure, on a column of silica gel(particle size 20-45μ; diameter 2 cm; volume 80 cm³), eluting with amixture of chloroform/methanol/aqueous ammonia (12/3/0.5 by volume).Fractions 8 to 20 were combined and then concentrated to dryness underthe same conditions as above. 1.37 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-4-carboxylatewere obtained in the form of a cream-colored foam.

[3833]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.10 to1.45 (mt: 3H); from 1.55 to 1.75 (mt: 1H); from 1.80 to 2.05 (mt: 4H);2.40 (mt: 2H); 2.72 (mt: 2H); 3.50 (s: 3H); 3.90 (s: 3H); 5.42 (broad t,J=6.5 Hz: 1H); 6.09 (mt: 1H); 7.45 (dd, J=9 and 3 Hz: 1H); 7.97 (d, J=9Hz: 1H); 8.15 (d, J=3 Hz: 1H); 8.67 (s: 1H).

Methyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)hydroxypropyl]-(tert-butyloxycarbonyl)piperidine carboxylate

[3834] A solution of 5 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylatein 400 cm³ of dimethyl sulfoxide and 120 cm³ of tert-butanol was stirredunder an oxygen-saturated atmosphere at a temperature in the region of20° C. After 5 minutes, a solution of 2.8 g of potassium tert-butoxidein 30 cm³ of tert-butanol was added to the reaction mixture. Aftersparging with oxygen for 2 hours, 300 cm³ of ice-cold water and 3.5 cm³of acetic acid were added cautiously. The aqueous phase was extractedwith twice 200 cm³ of dichloromethane. The organic phases were combinedand washed with 4 times 1 dm3 of water. The organic phase wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue was taken up in 200 cm³ of diethylether, filtered, washed with 20 cm³ of diethyl ether and then dried in adessicator under reduced pressure (0.1 kPa) at a temperature in theregion of 40° C. 3 g of methyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]-(tert-butyloxycarbonyl)piperidinecarboxylate were obtained in the form of a white solid melting at 222°C.

[3835]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): from 1.10 to1.50 (mt: 3H); 1.39 (s: 9H); 1.70 (mt: 1H); from 1.80 to 2.10 (mt: 4H);2.81 (mt: 2H); 3.69 (mt: 2H); 3.89 (s: 3H); 5.41 (dd, J=9 and 5 Hz: 1H);from 5.80 to 6.30 (broad unresolved peak: 1H); 7.44 (dd, J=9 and 3 Hz:1H); 7.95 (d, J=9 Hz: 1H); 8.16 (d, J=3 Hz: 1H); 8.65 (s: 1H); from12.00 to 12.90 (broad unresolved peak: 1H).

[3836] The 1-(2-bromoethoxy)-2,5-difluorobenzene was prepared asdescribed in Example 16.

[3837] The ethyl4-[3-(3-chloro-6-methoxyquinolinyl)-propyl]-1-(tert-butoxycarbonyl)piperidine-4-carboxylatewas prepared as described in Example 5.

EXAMPLE 50

[3838] Ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(thiazol-2-yloxy)ethyl]piperidine-4-carboxylatewas prepared.

[3839]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.05 (t, J=7 Hz:3H); 1.40 (very broad t, J=12 Hz: 2H); 1.53 (mt: 2H); 1.69 (mt: 2H);from 1.90 to 2.15 (mt: 4H); 2.64 (t, J=5.5 Hz: 2H); 2.70 (broad d,J=11.5 Hz: 2H); 3.16 (broad t, J=7.5 Hz: 2H); 3.96 (s: 3H); 4.01 (q, J=7Hz: 2H); 4.42 (t, J=5.5 Hz: 2H); 7.04 (d, J=3.5 Hz: 1H); 7.17 (d, J=3.5Hz: 1H); 7.37 (d, J=2.5 Hz: 1H); 7.46 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d,J=9 Hz: 1H); 8.67 (s: 1H).

4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-yloxy)ethyl]piperidine-4-carboxylicacid

[3840] A mixture of 0.68 g of ethyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-yloxy)-ethyl]piperidine-4-carboxylatein 7 cm³ of dioxane, 9 cm³ of methanol and 2 cm³ of aqueous 5N sodiumhydroxide solution was maintained at a temperature in the region of 60°C. for 20 hours. After cooling to about 20° C., the reaction mass wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was chromatographed under apressure of 50 kPa of argon, on a column of silica gel (particle size20-45μ; diameter 2.2 cm; mass 20 g), eluting with a mixture ofdichloromethane/methanol (70/30 by volume). The fractions containing theexpected product were combined and then concentrated to dryness underthe above conditions. The residue obtained was taken up in 5 cm³ ofethyl acetate, stirred for 1 hour at room temperature and then filteredand rinsed with 3 times 3 cm³ of ethyl acetate and then 3 times 3 cm³ ofpentane. 0.27 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-yloxy)-ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 188° C.

[3841]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.39 (broad t,J=12 Hz: 2H); from 1.50 to 1.65 (mt: 2H); 1.71 (mt: 2H); 1.98 (broad d,J=12 Hz: 2H); 2.12 (unresolved peak: 2H); from 2.60 to 2.85 (mt: 4H);3.17 (broad t, J=7.5 Hz: 2H); 3.96 (s: 3H); 4.45 (very broad t, J=5.5Hz: 2H); 7.05 (d, J=3.5 Hz: 1H); 7.18 (d, J=3.5 Hz: 1H); 7.37 (d, J==2.5Hz: 1H); 7.46 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.68 (s:1H); from 11.80 to 12.70 (broad unresolved peak: 1H).

EXAMPLE 514-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4,5-dihydrothiazol-2-ylthio)ethyl]piperidine-4-carboxylicacid

[3842] A mixture of 0.15 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4,5-dihydrothiazol-2-ylthio)ethyl]piperidine-4-carboxylatein 5 cm³ of dioxane, 5 cm³ of methanol and 1 cm³ of aqueous 5N sodiumhydroxide solution was maintained at a temperature in the region of 75°C. for 20 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was purified bychromatography under atmospheric pressure, on a column of silica gel(Bond Elut; particle size 70-200μ; mass 7 g), eluting with a mixture ofdichloromethane/methanol/aqueous ammonia (40/5/0.5 by volume). Thefractions containing the product were combined, concentrated to drynessunder reduced pressure (2 kPa) at a temperature in the region of 40° C.and then oven-dried under reduced pressure (10 kPa) at about 50° C. 0.1g of4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4,5-dihydrothiazol-2-ylthio)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3843]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.33 (very broadt, J=11.5 Hz: 2H); 1.61 (mt: 4H); from 1.90 to 2.10 (mt: 4H); from 2.45to 2.60 (mt: 2H); 2.63 (broad d, J=11.5 Hz: 2H); 3.05 (mt: 2H); 3.19 (t,J=6.5 Hz: 2H); 3.44 (t, J=8 Hz: 2H); 3.97 (s: 3H); 4.15 (t, J=8 Hz: 2H);7.35 (broad s: 1H); 7.40 (broad d, J=9 Hz: 1H); 7.97 (broad d, J=9 Hz:1H); 8.69 (broad s: 1H).

[3844] Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4,5-dihydrothiazol-2-ylthio)ethyl]piperidine-4-carboxylate

[3845] A mixture of 0.7 g of ethyl1-(2-chloroethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatedihydrochloride, 0.18 g of 2-mercaptothiazoline and 0.63 cm³ oftriethylamine in 10 cm³ of dimethylformamide was stirred under an inertatmosphere for 23 hours at a temperature in the region of 80° C. Aftercooling to about 20° C., the reaction mixture was taken up in water,extracted with ethyl acetate and washed with saturated sodium chloridesolution. The organic phase was dried over magnesium sulfate, filteredand then concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. The evaporation residue was added toa solution of 0.18 g of 2-mercaptothiazoline and 0.06 g of 10% sodiumhydride in 10 cm³ of dimethylformamide, and the mixture was then heatedat a temperature in the region of 80° C. for 15 hours. After cooling toabout 20° C., the reaction mixture was taken up in water, extracted withethyl acetate and washed with saturated sodium chloride solution. Theorganic phase was dried over magnesium sulfate, filtered and thenconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. The residue obtained was purified bychromatography under atmospheric pressure on a column of silica gel(particle size 70-200μ; diameter 2 cm; mass 40 g), eluting with amixture of dichloromethane/ethanol (95/5 by volume) and collecting10-cm³ fractions. Fractions 11 to 24 were combined and then concentratedto dryness under reduced pressure (2 kPa) at a temperature in the regionof 40° C. 0.15 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(4,5-dihydrothiazol-2-ylthio)ethyl]piperidine-4-carboxylatewas obtained in the form of a brown oil.

[3846]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, with addition of a fewdrops of CD₃COOD d4, δ in ppm): 1.06 (t, J=7 Hz: 3H); 1.41 (mt: 2H);from 1.50 to 1.70 (mt: 4H); 1.98 (broad d, J=13.5 Hz: 2H); 2.14 (broadt, J=11.5 Hz: 2H); 2.66 (t, J=7 Hz: 2H); 2.80 (very broad d, J=11.5 Hz:2H); 3.04 (broad t, J=6.5 Hz: 2H); 3.21 (t, J=7 Hz: 2H); 3.42 (t, J=8Hz: 2H); 3.94 (s: 3H); 3.97 (q, J=7 Hz: 2H); 4.12 (t, J=8 Hz: 2H); 7.32(d, J=2.5 Hz: 1H); 7.38 (dd, J=9 and 2.5 Hz: 1H); 7.96 (d, J=9 Hz: 1H);8.66 (d, J=1.5 Hz: 1H).

[3847] Ethyl1-(2-chloroethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatedihydro-chloride

[3848] 5.73 cm³ of thionyl chloride were added dropwise to a suspensionof 0.6 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylatein 10 cm³ of dichloromethane with stirring in the region of 20° C., andthe mixture was stirred for 24 hours at a temperature in the region of20° C. The reaction mixture was concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. The residuewas taken up in 3 times 30 cm³ of cyclohexane and evaporated to drynessas under the above conditions. 0.67 g of ethyl1-(2-chloroethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatedihydrochloride was obtained in the form of a beige-colored solid.

[3849]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.05 (t, J=7 Hz:3H); from 1.45 to 2.00 (mt: 6H); 2.19 (broad d, J=14 Hz: 2H); from 2.75to 2.95 (mt: 2H); 3.09 (mt: 2H); from 3.40 to 3.60 (mt: 4H); from 3.95to 4.15 (mt: 2H); 3.96 (s: 3H); 4.05 (q, J=7 Hz: 2H); 7.37 (d, J=2.5 Hz:1H); 7.42 (dd, J=9 and 2.5 Hz: 1H); 7.99 (d, J=9 Hz: 1H); 8.73 (broad s:1H); 10.00 (unresolved peak: 1H).

[3850] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylatewas prepared by analogy with the method described in Example 46.

EXAPLE 524-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid

[3851] A mixture of 0.8 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluoro-phenoxy)ethyl]piperidine-4-carboxylatein 50 cm³ of dioxane, 50 cm³ of methanol and 4.4 cm³ of aqueous 5Nsodium hydroxide solution was stirred at a temperature in the region of70° C. for 18 hours. A further 4.4 cm³ of aqueous 5N sodium hydroxidesolution were added to the reaction mixture, which was stirred for 6hours in the region of 70° C. After cooling to about 20° C., thereaction mass was concentrated to dryness under reduced pressure (1.1kPa) at a temperature in the region of 50° C. The residue was purifiedby chromatography under atmospheric pressure, on a column of silica gel(particle size 20-45μ; diameter 4 cm; height 20 cm), eluting with amixture of chloroform/methanol/aqueous ammonia (12/3/0.5 by volume) andcollecting 60-cm³ fractions. Fractions 8 to 19 were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and oven-dried under reduced pressure (10 kPa)at about 50° C. 0.59 g of4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyll-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid melting at about 120° C.

[3852]¹H NMR-Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.32 (very broadt, J=12 Hz: 2H); 1.59 (mt: 4H); 1.95 (broad d, J=12 Hz: 2H); 2.07 (broadt, J=11 Hz: 2H); 2.59 (t, J=5.5 Hz: 2H); 2.68 (very broad d, J=11 Hz:2H); 3.04 (mt: 2H); 3.95 (s: 3H); 4.03 (t, J=5.5 Hz: 2H); 6.97 (mt: 2H);7.34 (d, J=2.5 Hz: 1H); 7.39 (dd, J=9 and 2.5 Hz: 1H); 7.96 (d, J=9 Hz:1H); 8.69 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylate

[3853] A mixture of 0.62 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate,0.505 g of 5-(2-bromoethoxy)-1,2,3-trifluorobenzene, 0.34 g of potassiumiodide and 1.14 g of potassium carbonate in 80 cm³ of acetonitrile wasstirred under an inert atmosphere for 18 hours at a temperature in theregion of 70° C. After cooling to about 20° C., the suspension wasfiltered and the insoluble material was washed with 3 times 30 cm³ ofacetonitrile. The filtrate was concentrated to dryness under reducedpressure (2 kPa) at a temperature in the region of 40° C. Theevaporation residue was purified by chromatography under atmosphericpressure, on a column of silica gel (particle size 20-45μ; diameter 3cm; height 21 cm), eluting with ethyl acetate and collecting 40-cm³fractions. Fractions 9 to 24 were combined and then concentrated todryness under reduced pressure (2 kPa) at a temperature in the region of40° C. 0.8 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,4,5-trifluorophenoxy)ethyl]piperidine-4-carboxylatewas obtained in the form of a pale yellow viscous oil.

[3854]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 0.99 (t, J=7 Hz:3H); 1.37 (very broad t, J=12 Hz: 2H); from 1.45 to 1.70 (mt: 4H); from1.90 to 2.10 (mt: 4H); 2.59 (t, J=5.5 Hz: 2H); 2.69 (broad d, J=12 Hz:2H); 3.04 (broad t, J=7 Hz: 2H); 3.94 (s: 3H); 3.97 (q, J=7 Hz: 2H);4.03 (t, J=5.5 Hz: 2H); 6.97 (mt: 2H); 7.33 (d, J=2.5 Hz: 1H); 7.39 (dd,J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.69 (broad s: 1H).

[3855] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

[3856] The 5-(2-bromoethoxy)-1,2,3-trifluorobenzene was prepared byapplying the method described in Example 13.

EXAMPLE 534-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-ylthio)ethyl]piperidine-4-carboxylicacid

[3857] A mixture of 0.15 g of4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-ylthio)ethyl]-piperidine-4-carboxylatein 3 cm³ of dioxane, 3 cm³ of methanol and 1 cm³ of aqueous 5N sodiumhydroxide solution was stirred at a temperature in the region of 70° C.for 18 hours. After cooling to about 20° C., the reaction mass wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 50° C.

[3858] The residue was taken up in twice 20 cm³ of toluene and thenconcentrated to dryness as under the above conditions. The solid waspurified by chromatography under atmospheric pressure, on a column ofsilica gel (Bond Elut; particle size 70-200μ; mass 7 g), eluting with amixture of chloroform/methanol/aqueous ammonia (84/14/2 by volume) andcollecting 5-cm³ fractions. Fractions 8 to 19 were combined,concentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C. and then oven-dried under reduced pressure (to10 kPa) at about 50° C. 0.114 g of4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-yl-thio)ethyl]piperidine-4-carboxylicacid was obtained in the form of a white solid.

[3859]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.31 (broad t,J=12 Hz: 2H); 1.45 to 1.70 (mt: 4H); from 1.90 to 2.10 (mt: 4H); 2.58(t, J=7 Hz: 2H); 2.65 (broad d, J=12 Hz: 2H); 3.04 (mt: 2H); from 3.25to 3.45 (mt, 2H); 3.95 (s: 3H); 7.34 (d, J=2.5 Hz: 1H); 7.39 (dd, J=9and 2.5 Hz: 1H); 7.63 (d, J=3.5 Hz: 1H); 7.71 (d, J=3.5 Hz: 1H); 7.96(d, J=9 Hz: 1H); 8.68 (d, J=1 Hz: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-ylthio)ethyl]piperidine-4-carboxylate

[3860] A mixture of 0.65 g of ethyl1-(2-chloroethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatedihydrochloride, 0.183 g of 2-mercaptothiazole, 0.21 g of potassiumiodide and 0.88 g of potassium carbonate in 50 cm³ of acetonitrile wasstirred under an inert atmosphere for 18 hours at a temperature in theregion of 70° C. After cooling to about 20° C., the suspension wasfiltered and the insoluble material was washed with acetonitrile. Thefiltrate was concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C.

[3861] The evaporation residue was taken up in a mixture of ethylacetate/40-60° C. petroleum ether (8/2 by volume) and filtered, and thefiltrate was purified by chromatography under atmospheric pressure on acolumn of silica gel (particle size 70-200μ; diameter 1.5 cm; mass 100g), eluting with ethyl acetate/40-60° C. petroleum ether (8/2 by volume)and collecting 15-cm³ fractions. The fractions 41 to 100 were combinedand then concentrated to dryness under reduced pressure (2 kPa) at atemperature in the region of 40° C. 0.15 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-ylthio)ethyl]piperidine-4-carboxylatewas obtained in the form of a thick yellow oil.

[3862]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.00 (t, J=7 Hz:3H); 1.36 (broad t, J=11.5 Hz: 2H); from 1.45 to 1.70 (mt: 4H); from1.85 to 2.10 (mt: 4H); 2.59 (t, J=7 Hz: 2H); 2.68 (broad d, J=12 Hz:2H); 3.05 (very broad t, J=7 Hz: 2H); 3.33 (mt: 2H); 3.96 (s: 3H); 3.98(q, J=7 Hz: 2H); 7.35 (d, J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H);7.64 (d, J=3.5 Hz: 1H); 7.72 (d, J=3.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H);8.70 (d, J=1 Hz: 1H).

[3863] The ethyl1-(2-chloroethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatedihydrochloride was prepared as described in Example 51.

EXAMPLE 54

[3864]4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylicacid

[3865] A mixture of 0.13 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylatein 2 cm³ of dioxane, 2 cm³ of methanol and 1.32 cm³ of aqueous 5N sodiumhydroxide solution was maintained at a temperature in the region of 70°C. for 18 hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of 40° C.

[3866] The residue obtained was taken up in 10 cm³ of water, acidifiedwith acetic acid and extracted with ethyl acetate, allowed to separateby settling and then filtered and rinsed with twice 10 cm³ of ethanol.0.12 g of4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylicacid was obtained in the form of a white solid melting at 240° C.

[3867]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.35 (broad t,J=11.5 Hz: 2H); from 1.50 to 1.75 (mt: 4H); from 1.85 to 2.10 (mt: 4H);2.63 (broad d, J=11.5 Hz: 2H); from 2.95 to 3.15 (mt: 4H); 3.96 (s, 3H);6.26 (dt, J=16 and 7 Hz: 1H); 6.50 (d, J=16 Hz: 1H); from 7.10 to 7.50(mt: 7H); 8.06 (d, J=9 Hz: 1H); 8.69 (broad s: 1H).

Ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylate

[3868] 77 mg of borane-pyridine complex were added to a mixture of 0.31g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylateand 0.1 cm³ of trans-cinnamaldehyde in 10 cm³ of ethanol. The reactionmixture was maintained at a temperature in the region of 77° C. for 22hours. After cooling to about 20° C., the reaction mixture wasconcentrated to dryness under reduced pressure (2 kPa) at a temperaturein the region of ₄₀° C.

[3869] The residue obtained was taken up in 10 cm³ of water, extractedwith twice 10 cm³ of dichloromethane, dried over magnesium sulfate,filtered and then concentrated to dryness under the above conditions.The residue obtained was chromatographed under a pressure of 60 kPa ofargon, on a column of silica gel (particle size 70-200μ; diameter 2.5cm; mass 20 g), eluting with 500 cm³ of a mixture of ethylacetate/cyclohexane (40/60 by volume) and then of a mixture ofdichloromethane/methanol (95/5 by volume). The fractions containing theexpected product were combined and then concentrated to dryness underthe above conditions. 0.13 g of ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylatewas obtained in the form of a viscous oil.

[3870]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.01 (t, J=7 Hz:3H); 1.40 (broad t, J=11.5 Hz: 2H); from 1.45 to 1.75 (mt: 4H); from1.90 to 2.05 (mt: 4H); 2.65 (very broad d, J=12 Hz: 2H); 3.02 (d, J=7Hz: 2H); 3.05 (mt: 2H); 3.96 (s: 3H); 3.97 (q, J=7 Hz: 2H); 6.25 (dt,J=16 and 7 Hz: 1H); 6.51 (d, J=16 Hz: 1H); from 7.15 to 7.50 (mt: 7H);7.96 (d, J=9 Hz: 1H); 8.70 (d, J=1 Hz: 1H).

[3871] The ethyl4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylatewas prepared as described in Example 11.

EXAMPLE 554-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-hydroxamicacid

[3872] A solution of 0.1 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-tert-butoxycarboxamidein 2 cm³ of trifluoroacetic acid was left for 60 days at a temperaturein the region of 20° C. The solution was evaporated off under reducedpressure (2 kPa) at a temperature in the region of 40° C. and thenpurified by chromatography under atmospheric pressure on Bond Elutsilica (particle size 70-200μ; volume 25 cm 3), eluting with a mixtureof dichloromethane/methanol/aqueous ammonia (40/5/0.3 by volume). Thefractions containing the product were combined and then evaporated underthe conditions described above. 0.036 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-hydroxamicacid was obtained in the form of a colorless oil.

[3873]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.33 (mt: 2H);1.51 (mt: 2H); from 1.60 to 1.80 (mt: 4H); from 1.90 to 2.10 (mt: 4H);2.18 (t, J=7 Hz: 2H); from 2.45 to 2.65 (mt: 4H); 3.12 (broad t, J=7.5Hz: 2H); 3.96 (s: 3H); from 7.15 to 7.25 (mt: 3H); 7.28 (t mt, J=7.5 Hz:2H); 7.36 (d, J=2.5 Hz: 1H); 7.45 (dd, J=9 and 2.5 Hz: 1H); 7.96 (d, J=9Hz: 1H); 8.56 (unresolved peak: 1H); 8.67 (s: 1H); 10.37 (unresolvedpeak: 1H).

4-[3-(3-Chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-tert-butoxyamide

[3874] A mixture of 0.5 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylicacid, 0.175 g of 1-hydroxybenzotriazole hydrate, 0.498 g of1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, 0.58 cm³of triethylamine and 0.4 g of O-tert-butylhydroxylamine was stirred for48 hours at a temperature in the region of 20° C. The reaction mediumwas diluted with 50 cm³ of water, stirred and the phases were thenseparated by settling. The aqueous phase was extracted with twice 25 cm³of dichloromethane and the organic extracts were combined, dried overmagnesium sulfate, filtered and then evaporated under reduced pressure(2 kPa) at a temperature in the region of 40° C.

[3875] The residue obtained was purified by chromatography underatmospheric pressure, on a column of silica gel (particle size 20-45μ;diameter 2.5 cm; mass 18 g), eluting with a mixture ofdichloromethane/methanol/aqueous ammonia (40/5/0.2 by volume) Thefractions containing the product were combined and then evaporated underthe conditions described above. 0.27 g of4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-tert-butoxyamidewas obtained.

[3876]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.09 (s: 9H);1.35 (mt: 2H); 1.54 (mt: 2H); 1.67 (mt: 4H); 1.95 (broad t, J=11 Hz:2H); 2.08 (broad d, J=13.5 Hz: 2H); 2.19 (t, J=7 Hz: 2H); from 2.50 to2.65 (mt: 4H); 3.14 (broad t, J=7.5 Hz: 2H); 3.98 (s: 3H); from 7.10 to7.25 (mt: 3H); 7.27 (broad t, J=7.5 Hz: 2H); 7.36 (d, J=2.5 Hz: 1H);7.45 (dd, J=9 and 2.5 Hz: 1H); 7.96 (d, J=9 Hz: 1H); 8.68 (s: 1H); 10.06(broad s: 1H).

[3877] Benzyl4-[3-(3-chloro-6-methoxyquinolin-4-yl)-propyl]-1-(3-phenylpropyl)piperidine-4-carboxylatewas prepared as described in Example 4.

EXAMPLE 564-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,5-difluorophenyl)prop-2-enyl]piperidine-4-carboxylicacid hydrochloride

[3878] Working in a manner analogous to that of Example 54,4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[3-(2,5-difluorophenyl)prop-2-enyl]piperidine-4-carboxylicacid hydrochloride was prepared.

[3879]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CD₃COOD-d₄ at a temperature of 383 K, δ in ppm): 1.73 (mt: 6H); 2.22(broad d, J=14 Hz: 2H); 3.01 (unresolved peak: 2H); 3.11 (broad t, J=7Hz: 2H); 3.42 (very broad d, J=12 Hz: 2H); 3.94 (d, J=7 Hz: 2H); 3.98(s: 3H) ; 6.48 (dt, J=16.5 and 7 Hz: 1H); 6.93 (d, J=16.5 Hz: 1H); from7.10 to 7.30 (mt: 2H); 7.35 (broad s: 1H); 7.40 (dd, J=9 and 2.5 Hz:1H); 7.44 (mt: 1H); 7.98 (d, J=9 Hz: 1H); 8.64 (broad s: 1H).

EXAMPLE 574-[3-(3-Fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid

[3880] Working in a manner analogous to that of Example 55,4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-hydroxamicacid was prepared.

[3881]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm): 1.31 (very broadt, J=12.5 Hz: 2H); from 1.45 to 1.70 (mt: 4H); 2.02 (broad d, J=12.5 Hz:2H); 2.10 (broad t, J=11 Hz: 2H); from 2.55 to 2.75 (mt: 4H); 3.00 (mt:2H); 3.97 (s: 3H); 4.12 (t, J=5.5 Hz: 2H); 6.75 (mt: 1H); 7.14 (mt: 1H)7.24 (mt: 1H); 7.33 (d, J=3 Hz: 1H); 7.40 (dd, J=9 and 3 Hz: 1H); 7.96(d, J=9 Hz: 1H); 8.63 (unresolved peak: 1H); 8.70 (d, J=0.5 Hz: 1H);10.40 (unresolved peak: 1H).

EXAMPLE 581-Cinnamyl-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-piperidine-4-hydroxamicacid

[3882] Working in a manner analogous to that of Example 55,1-cinnamyl-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-piperidine-4-hydroxamicacid was prepared.

[3883]¹H NMR Spectrum (400 MHz, (CD₃)₂SO-d₆ with addition of a few dropsof CD₃COOD-d₄ at a temperature of 373 K, δ in ppm): from 1.50 to 1.75(mt: 6H); 2.23 (broad d, J=14 Hz: 2H); 2.81 (broad t, J=11.5 Hz: 2H);3.04 (mt: 2H); 3.22 (broad d, J=11.5 Hz: 2H); 3.69 (d, J=7 Hz: 2H); 3.97(s: 3H); 6.24 (dt, J=16 and 7 Hz: 1H); 6.78 (d, J=16 Hz: 1H); from 7.20to 7.50 (mt: 7H); 7.96 (d, J=9 Hz: 1H); 8.62 (broad s: 1H).

EXAMPLE 59 Sodium4-[3-(3-chloro-6-trifluoromethylquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylate

[3884] Working in a manner analogous to that of Example 1, sodium4-[3-(3-chloro-6-trifluoromethylquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenoxy)ethyl]piperidine-4-carboxylatewas prepared.

[3885]¹H NMR Spectrum (300 MHz, (CD₃)₂SO-d₆, δ in ppm):

[3886] 1.09 (very broad t, J=11.5 Hz: 2H); from 1.40 to 1.70 (mt: 4H);1.98 (broad d, J=11.5 Hz: 2H); 2.14 (t, J=10.5 Hz: 2H); from 2.50 to2.70 (mt: 4H); 3.22 (broad t, J=7 Hz: 2H); 4.10 (t, J=5.5 Hz: 2H); 6.74(mt: 1H); 7.12 (mt: 1H); 7.23 (mt: 1H); 8.06 (broad d, J=9 Hz: 1H); 8.26(d, J=9 Hz: 1H); 8.26 (d, J=9 Hz: 1H); 8.54 (broad s: 1H); 9.00 (s: 1H).

[3887] The present invention also relates to pharmaceutical compositionscontaining at least one heterocyclylalkyl-piperidine derivativeaccording to the invention, where appropriate in the form of a salt, inpure form, or in the form of a combination with one or more compatibleand pharmaceutically acceptable diluents and/or adjuvants.

[3888] The compositions according to the invention may be used orally,parenterally, topically, rectally, or as aerosols.

[3889] Solid compositions for oral administration which were optionallyused include tablets, pills, gel capsules, powders or granules. In thesecompositions, the active product according to the invention mayoptionally be mixed with one or more inert diluents or adjuvants, suchas sucrose, lactose or starch. These compositions may comprisesubstances other than diluents, for example a lubricant such asmagnesium stearate or a coating intended for controlled release.

[3890] Liquid compositions for oral administration which may be usedinclude pharmaceutically acceptable solutions, suspensions, emulsions,syrups and elixirs containing inert diluents such as water or liquidparaffin. These compositions may also comprise substances other thandiluents, for example wetting, sweetening or flavoring products.

[3891] The compositions for parenteral administration may be sterilesolutions or emulsions. Solvents or vehicles which may be used includewater, propylene glycol, a polyethylene glycol, plant oils, inparticular olive oil, and injectable organic esters, for example ethyloleate. These compositions may also contain adjuvants, in particularwetting agents, isotonic agents, emulsifiers, dispersants andstabilizers.

[3892] The sterilization may be carried out in several ways, for exampleusing a bacteriological filter, by irradiation or by heating. Thecompositions may also be prepared in the form of sterile solidcompositions which may be dissolved at the time of use in sterile wateror any other injectable sterile medium.

[3893] The compositions for topical administration may be, for example,creams, ointments, lotions or aerosols.

[3894] The compositions for rectal administration were suppositories orrectal capsules which contain, besides the active principle, excipientssuch as cocoa butter, semi-synthetic glycerides or polyethylene glycols.

[3895] The compositions may also be aerosols. For use in the form ofliquid aerosols, the compositions may be stable sterile solutions orsolid compositions dissolved at the time of use in apyrogenic sterilewater, in saline or any other pharmaceutically acceptable vehicle. Foruse in the form of dry aerosols intended to be inhaled directly, theactive principle was finely divided and combined with a water-solublesolid diluent or vehicle with a particle size of from 30 to 80 μm, forexample dextran, mannitol or lactose.

[3896] In human therapy, the novel heterocyclylalkyl-piperidinederivatives according to the invention were particularly useful in thetreatment of infections of bacterial origin. The doses depend on thedesired effect and on the duration of the treatment. The doctor willdetermine the dosage she or he considers most appropriate as a functionof the treatment, depending on the age, weight, degree of infection andother factors specific to the individual to be treated. Generally, thedoses were between 750 mg and 3 g of active product taken 2 or 3 times aday orally or between 400 mg and 1.2 g intravenously for an adult.

1. A compound of general formula (I):

wherein: X₁, X₂, X₃, X₄ and X₅ are >C—R′₁ to >C—R′₅, respectively, or,alternatively, not more than one of X₁, X₂, X₃, X₄, and X₅ is a nitrogenatom; R₁, R′₁, R′₂, R′₃, R′₄, and R′₅ are identical or different, andeach independently is: a hydrogen or halogen atom or an alkyl,cycloalkyl, phenyl, phenylthio, mono- or bicyclic aromatic heterocyclylor heterocyclylthio, hydroxyl, alkyloxy, trifluoromethoxy, alkylthio,trifluoromethylthio, cycloalkyloxy, cycloalkylthio, cyano, carboxyl,alkyloxycarbonyl, cycloalkyloxycarbonyl, —NRaRb or —CONRaRb radical (forwhich Ra and Rb are hydrogen, alkyl, cycloalkyl, phenyl, mono- orbicyclic aromatic heterocyclyl, or Ra and Rb form, together with thenitrogen atom to which they are attached, a 5- or 6-membered heterocyclewhich can optionally contain another heteroatom chosen from O, S and Nand, where appropriate, bearing an alkyl, phenyl or mono- or bicyclicaromatic heterocyclyl substituent on the nitrogen atom or, whereappropriate, the sulfur atom of which is oxidized in the form ofsulfinyl or sulfonyl), or represent a methylene radical substituted withfluoro, hydroxyl, alkyloxy, alkylthio, cycloalkyloxy, cycloalkylthio,phenyl, mono- or bicyclic aromatic heterocyclyl, carboxyl,alkyloxycarbonyl, cycloalkyloxycarbonyl, —NRaRb or —CONRaRb for which Raand Rb are defined as above, or represent phenoxy, heterocyclyloxy,benzyloxy, heterocyclylmethyloxy, or, alternatively, R₁ isdifluoromethoxy, or a radical of structure —C_(m)F_(2m+1),—SC_(m)F_(2m+1), or —OC_(m)F_(2m+1) wherein m is an integer from 1 to 6;or alternatively, R′₅ is trifluoroacetyl; R₂ is: carboxyl,alkyloxycarbonyl, cycloalkyloxycarbonyl, cyano, —CONRaRb, wherein Ra andRb are, respectively, hydrogen, alkyl, cycloalkyl, phenyl, mono- orbicyclic aromatic heterocyclyl, or Ra or Rb each is hydroxyl, alkyloxy,cycloalkyloxy, or Ra and Rb form, together with the nitrogen atom towhich they are attached, a 5- or 6-membered heterocycle which canoptionally contain another heteroatom chosen from O, S and N and, whereappropriate, bearing an alkyl, phenyl or mono- or bicyclic aromaticheterocyclyl substituent on the nitrogen atom or, where appropriate, thesulfur atom of which is oxidized in the form of sulfinyl or sulfonyl; orR₂ is hydroxymethyl, alkyl containing 1 or 2 carbon atoms substitutedwith carboxyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, cyano, or—CONRaRb, wherein Ra and Rb are defined as above; or R₂ is —CF₂-Rc,—C(CH₃)₂-Rc, —CO-Rc, —CHOH-Rc, —C(cycloalkyl)-Rc, or —CH═CH-Rc, whereinRc is carboxyl, alkyloxycarbonyl, cycloalkyloxy-carbonyl, or —CONRaRbwherein Ra and Rb are defined as above; R₃ is a phenyl, mono- orbicyclic aromatic heterocyclyl or alk-R°₃ radical, wherein alk is analkyl radical, and R°₃ is hydrogen, halogen, hydroxyl, alkyloxy,alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino,cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylsulfinyl,cycloalkylsulfonyl, cycloalkylamino, N-cycloalkyl-N-alkylamino,—N-(cycloalkyl)₂, acyl, cycloalkylcarbonyl, phenyl, phenoxy, phenylthio,phenylsulfinyl, phenylsulfonyl, phenylamino, N-alkyl-N-phenylamino,N-cycloalkyl-N-phenylamino, —N-(phenyl)₂, phenylalkyloxy,phenylalkylthio, phenylalkylsulfinyl, phenylalkylsulfonyl,phenylalkylamino, N-alkyl-N-phenylaminoalkyl,N-cycloalkyl-N-phenylalkylamino, benzoyl, mono- or bicyclic aromaticheterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylsulfinyl,heterocyclylsulfonyl, heterocyclylamino, N-alkyl-N-heterocyclylamino,N-cycloalkyl-N-heterocyclylamino, heterocyclylcarbonyl,heterocyclylalkyloxy, heterocyclylalkylthio, heterocyclylalkylsulfinyl,heterocyclylalkylsulfonyl, heterocyclylalkylamino,N-alkyl-N-heterocyclylaminoalkyl,N-cycloalkyl-N-heterocyclylaminoalkyl,carboxyl, alkyloxycarbonyl,—NRaRb, or —CO—NRaRb, wherein Ra and Rb are defined as above in thedefinition of R₂ and wherein any heterocyclyl mentioned above is mono-or bicyclic aromatic; or alternatively R°₃ is —CR′b=CR′c-R′a, whereinR′a is phenyl, phenylalkyl, heterocyclyl, or heterocyclylalkyl,phenoxyalkyl, phenylthioalkyl, phenylsulfinylalkyl, phenylsulfonylalkyl,phenylaminoalkyl, N-alkyl-N-phenylaminoalkyl, heterocyclyloxyalkyl,heterocyclylthioalkyl, heterocyclylsulfinylalkyl,heterocyclylsulfonylalkyl, heterocyclylaminoalkyl,N-alkyl-N-heterocyclylaminoalkyl, heterocyclylthio,heterocyclylsulfinyl, heterocyclylsulfonyl, phenylthio, phenylsulfinyl,or phenylsulfonyl, wherein any heterocyclyl mentioned above is mono- orbicyclic aromatic, and R′b and R′c are hydrogen, alkyl or cycloalkyl; oralternatively R°₃ is a radical —C≡C-Rd wherein Rd is alkyl, phenyl,phenylalkyl, phenoxyalkyl, phenylthioalkyl, N-alkyl-N-phenylaminoalkyl,heterocyclyl, heterocyclylalkyl, heterocyclyloxyalkyl,heterocyclylthioalkyl, heterocyclylaminoalkyl,N-alkyl-N-heterocyclylaminoalkyl, wherein any heterocyclyl mentionedabove is mono- or bicyclic aromatic; or alternatively R°₃ is a—CF₂-phenyl, or mono- or bicyclic aromatic —CF₂-heterocyclyl radical, Yis a radical >CH—Re, wherein Re is hydrogen, fluoro, hydroxyl, alkyloxy,cycloalkyloxy, carboxyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, —NRaRbor —CO—NRaRb, wherein Ra and Rb are defined as above for R₂, or one is ahydrogen atom and the other is an alkyloxycarbonyl, acyl,cycloalkylcarbonyl, benzoyl or heterocyclylcarbonyl radical, wherein anyheterocyclyl portion is mono- or bicyclic aromatic; or alternatively Yis a difluoromethylene, carbonyl, hydroxyiminomethylene,alkyloxyiminomethylene, or cycloalkyloxyiminomethylene radical, or a1,1-cycloalkylene radical containing 3 to 6 carbon atoms; and n is aninteger from 0 to 4; wherein any phenyl, benzyl, benzoyl or heterocyclylradical or portion mentioned above are unsubstituted, or substituted onthe ring with 1 to 4 substituents independently chosen from halogen,hydroxyl, alkyl, alkyloxy, alkyloxyalkyl, haloalkyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, carboxyl, alkyloxycarbonyl,cyano, alkylamino, —NRaRb wherein Ra and Rb are defined as above,phenyl, hydroxyalkyl, alkylthioalkyl, alkylsulfinylalkyl andalkylsulfonylalkyl, wherein any alkyl or acyl radical or portion, unlessotherwise indicated, comprises from 1 to 10 carbon atoms in a straightor branched chain, and any cycloalkyl radical comprises from 3 to 6carbon atoms; in any enantiomeric or diastereoisomeric form, in any synor anti form, or any salt thereof, or mixture of any of the foregoing inany ratio.
 2. A compound as claimed in claim 1, wherein X₁, X₂, X₃, X₄,and X₅ are, respectively, >C—R′₁ to >C—R′₅, or alternatively not morethan one of them is a nitrogen atom; R₁, R′₁, R′₂, R′₃, R′₄ and R′₅ areidentical or different, and each is: a hydrogen or halogen atom or analkyl or alkyloxy radical, or is a methylene radical substituted withalkyloxy; R₂ is carboxyl, alkyloxycarbonyl or —CONRaRb, wherein Ra is ahydrogen atom and Rb is a hydrogen atom or a hydroxyl radical; or R₂ ishydroxymethyl, alkyl containing 1 or 2 carbon atoms substituted withcarboxyl, or alkyloxycarbonyl; R₃ is a radical alk-R°₃ wherein alk is analkyl radical, and R°₃ is hydrogen, cycloalkyl, cycloalkylthio, phenyl,phenoxy, phenylthio, phenylamino, heterocyclyloxy or heterocyclylthio,or alternatively R°₃ is —CR′b=CR′c-R′a wherein R′a is phenyl, andwherein R′b and R′c are hydrogen; Y is a radical >CH—Re, wherein Re ishydrogen, fluoro, or hydroxyl; n is an integer from 2 to 3; wherein anyphenyl or heterocyclyl radical or portion is unsubtituted, or issubstituted on the ring with from 1 to 4 halogens, and wherein any alkylor acyl radical or portion, unless otherwise indicated, comprises from 1to 10 carbon atoms in a straight or branched chain, and any cycloalkylradical comprises from 3 to 6 carbon atoms; in any enantiomeric ordiastereoisomeric form, in any syn or anti form, or any salt thereof, ormixture of any of the foregoing in any ratio. 3.4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-yl)thioethyl]piperidine-4-carboxylicacid, or any salt thereof. 4.4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylicacid, or any salt thereof. 5.4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiazol-2-thioethyl)piperidine-4-carboxylicacid, or any salt thereof. 6.1-(2-cyclopentylthioethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylicacid, or any salt thereof. 7.4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylallyl)piperidine-4-carboxylicacid, or any salt thereof.
 8. A process for preparing a compound asclaimed in claim 1, comprising: coupling a chain R₃ as defined in claim1 with a compound of general formula (II):

wherein X₁, X₂, X₃, X₄, X₅, R₁, R₂, Y and n are as defined in claim 1;optionally protecting R₂ when R₂ comprises a carboxyl or amino radical;optionally removing said protection from R₂; optionally separating anyenantiomeric or diastereoisomeric form, any syn or anti form, or anysalt thereof; and optionally converting a product obtained into a saltthereof.
 9. A process as claimed in claim 8, wherein said coupling of achain R₃ with a compound of general formula (II) occurs with a compoundof general formula: R₃—X wherein R₃ is defined as above, and X is ahalogen atom, a methylsulfonyl radical, a trifluoromethylsulfonylradical, or a p-toluenesulfonyl radical.
 10. A process as claimed inclaim 8, wherein R₃ is a radical -alk-R°₃, wherein alk is an alkylradical, and R°₃ is a radical —C≡C-Rd, wherein Rd is phenyl,phenylalkyl, heterocyclyl or mono- or bicyclic aromaticheterocyclylalkyl; comprising: coupling an alkynyl halide, HC≡C-alk-X,wherein alk is defined as above, and X is a halogen atom; andsubstituting the chain with a phenyl, phenylalkyl, heterocyclyl orheterocyclylalkyl radical.
 11. A process as claimed in claim 9, whereinR₃ is a radical -alk-R°₃, wherein alk is an alkyl radical, and R°₃ is aradical —C≡C-Rd, wherein Rd is phenyl, phenylalkyl, heterocyclyl ormono- or bicyclic aromatic heterocyclylalkyl; comprising: coupling analkynyl halide, HC≡C-alk-X, wherein alk is defined as above, and X is ahalogen atom; and substituting the chain with a phenyl, phenylalkyl,heterocyclyl or heterocyclylalkyl radical.
 12. A process as claimed inclaim 8, wherein: R₃ is a radical -alk-R°₃, wherein alk is an alkylradical, and R°₃ is a phenoxy, phenylthio, phenylamino, heterocyclyloxy,heterocyclylthio or heterocyclylamino radical in which the heterocyclylportion is aromatic; comprising constructing the chain stepwise by:condensing a chain HO-alk-X wherein X is a halogen atom; obtaining ahydroxyalkyl chain; converting the hydroxyalkyl chain into a haloalkyl,methanesulfonylalkyl, or p-toluenesulfonylalkyl chain by known methods;and reacting the chain in basic medium with an aromatic derivative ofstructure Ar-ZH, wherein Ar is a phenyl or aromatic heterocyclylradical, and Z is a sulfur, oxygen, or nitrogen atom.
 13. A process asclaimed in claim 9, wherein: R₃ is a radical -alk-R°₃, wherein alk is analkyl radical, and R°₃ is a phenoxy, phenylthio, phenylamino,heterocyclyloxy, heterocyclylthio or heterocyclylamino radical in whichthe heterocyclyl portion is aromatic, comprising constructing the chainstepwise by: condensing a chain HO-alk-X wherein X is a halogen atom;obtaining a hydroxyalkyl chain; converting the hydroxyalkyl chain into ahaloalkyl, methanesulfonylalkyl, or p-toluenesulfonylalkyl chain byknown methods; and reacting the chain in basic medium with an aromaticderivative of structure Ar-ZH, wherein Ar is a phenyl or aromaticheterocyclyl radical, and Z is a sulfur, oxygen, or nitrogen atom.
 14. Apharmaceutical composition, comprising at least one compound accordingto claim 1, alone, or in combination with one or more pharmaceuticallyacceptable adjuvants or diluents.
 15. A pharmaceutical composition,comprising at least one compound according to claim 3, alone, or incombination with one or more pharmaceutically acceptable adjuvants ordiluents.
 16. A pharmaceutical composition, comprising at least onecompound according to claim 4, alone, or in combination with one or morepharmaceutically acceptable adjuvants or diluents.
 17. A pharmaceuticalcomposition, comprising at least one compound according to claim 5,alone, or in combination with one or more pharmaceutically acceptableadjuvants or diluents.
 18. A pharmaceutical composition, comprising atleast one compound according to claim 6, alone, or in combination withone or more pharmaceutically acceptable adjuvants or diluents.
 19. Apharmaceutical composition, comprising at least one compound accordingto claim 7, alone, or in combination with one or more pharmaceuticallyacceptable adjuvants or diluents.